Perfume systems

ABSTRACT

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of U.S. application Ser. No.12/628,255, filed Dec. 1, 2009, which claims priority under 35 U.S.C.§119(e) to U.S. Provisional Application Ser. No. 61/118,720 filed Dec.1, 2008.

FIELD OF INVENTION

The present application relates to perfume raw materials, perfumedelivery systems and consumer products comprising such perfume rawmaterials and/or such perfume delivery systems, as well as processes formaking and using such perfume raw materials, perfume delivery systemsand consumer products.

BACKGROUND OF THE INVENTION

Consumer products may comprise one or more perfumes and/or perfumedelivery systems that can provide a desired scent to such product and/ora situs that is contacted with such a product and/or mask an undesirableodor. While current perfumes and perfume delivery systems providedesirable odors, consumers continue to seek products that have scentsthat may be longer lasting and that are tailored to their individualdesires (see for example USPA 2007/0275866 A1 and U.S. patentapplication Ser. No. 12/133,866)—unfortunately the pool of perfume rawmaterials and perfume delivery systems that is available is still toolimited to completely meet the perfume community's needs. Thus,perfumers need an ever larger pool of perfume raw materials and perfumedelivery systems.

Applicants believe that the perfume raw materials and compositions,including the delivery systems, disclosed herein expand the perfumecommunity's options, as such perfume raw materials can providevariations on character and such compositions can provide desired odorprofiles.

SUMMARY OF THE INVENTION

The present application relates to perfume raw materials, perfumesystems and consumer products comprising such perfume raw materialsand/or such perfume systems, as well as processes for making and usingsuch perfume raw materials, perfume systems and consumer products.

DETAILED DESCRIPTION OF THE INVENTION

Definitions

As used herein “consumer product” means baby care, beauty care, fabric &home care, family care, feminine care, health care, snack and/orbeverage products or devices generally intended to be used or consumedin the form in which it is sold. Such products include but are notlimited to diapers, bibs, wipes; products for and/or methods relating totreating hair (human, dog, and/or cat), including, bleaching, coloring,dyeing, conditioning, shampooing, styling; deodorants andantiperspirants; personal cleansing; cosmetics; skin care includingapplication of creams, lotions, and other topically applied products forconsumer use including fine fragrances; and shaving products, productsfor and/or methods relating to treating fabrics, hard surfaces and anyother surfaces in the area of fabric and home care, including: air careincluding air fresheners and scent delivery systems, car care,dishwashing, fabric conditioning (including softening and/or freshing),laundry detergency, laundry and rinse additive and/or care, hard surfacecleaning and/or treatment including floor and toilet bowl cleaners, andother cleaning for consumer or institutional use; products and/ormethods relating to bath tissue, facial tissue, paper handkerchiefs,and/or paper towels; tampons, feminine napkins; products and/or methodsrelating to oral care including toothpastes, tooth gels, tooth rinses,denture adhesives, tooth whitening; over-the-counter health careincluding cough and cold remedies, pain relievers, RX pharmaceuticals,pet health and nutrition; processed food products intended primarily forconsumption between customary meals or as a meal accompaniment(non-limiting examples include potato chips, tortilla chips, popcorn,pretzels, corn chips, cereal bars, vegetable chips or crisps, snackmixes, party mixes, multigrain chips, snack crackers, cheese snacks,pork rinds, corn snacks, pellet snacks, extruded snacks and bagelchips); and coffee.

As used herein, the term “cleaning and/or treatment composition” is asubset of consumer products that includes, unless otherwise indicated,beauty care, fabric & home care products. Such products include, but arenot limited to, products for treating hair (human, dog, and/or cat),including, bleaching, coloring, dyeing, conditioning, shampooing,styling; deodorants and antiperspirants; personal cleansing; cosmetics;skin care including application of creams, lotions, and other topicallyapplied products for consumer use including fine fragrances; and shavingproducts, products for treating fabrics, hard surfaces and any othersurfaces in the area of fabric and home care, including: air careincluding air fresheners and scent delivery systems, car care,dishwashing, fabric conditioning (including softening and/or freshing),laundry detergency, laundry and rinse additive and/or care, hard surfacecleaning and/or treatment including floor and toilet bowl cleaners,granular or powder-form all-purpose or “heavy-duty” washing agents,especially cleaning detergents; liquid, gel or paste-form all-purposewashing agents, especially the so-called heavy-duty liquid types; liquidfine-fabric detergents; hand dishwashing agents or light dutydishwashing agents, especially those of the high-foaming type; machinedishwashing agents, including the various tablet, granular, liquid andrinse-aid types for household and institutional use; liquid cleaning anddisinfecting agents, including antibacterial hand-wash types, cleaningbars, mouthwashes, denture cleaners, dentifrice, car or carpet shampoos,bathroom cleaners including toilet bowl cleaners; hair shampoos andhair-rinses; shower gels, fine fragrances and foam baths and metalcleaners; as well as cleaning auxiliaries such as bleach additives and“stain-stick” or pre-treat types, substrate-laden products such as dryeradded sheets, dry and wetted wipes and pads, nonwoven substrates, andsponges; as well as sprays and mists all for consumer or/andinstitutional use; and/or methods relating to oral care includingtoothpastes, tooth gels, tooth rinses, denture adhesives, toothwhitening.

As used herein, the term “fabric and/or hard surface cleaning and/ortreatment composition” is a subset of cleaning and treatmentcompositions that includes, unless otherwise indicated, granular orpowder-form all-purpose or “heavy-duty” washing agents, especiallycleaning detergents; liquid, gel or paste-form all-purpose washingagents, especially the so-called heavy-duty liquid types; liquidfine-fabric detergents; hand dishwashing agents or light dutydishwashing agents, especially those of the high-foaming type; machinedishwashing agents, including the various tablet, granular, liquid andrinse-aid types for household and institutional use; liquid cleaning anddisinfecting agents, including antibacterial hand-wash types, cleaningbars, car or carpet shampoos, bathroom cleaners including toilet bowlcleaners; and metal cleaners, fabric conditioning products includingsoftening and/or freshing that may be in liquid, solid and/or dryersheet form; as well as cleaning auxiliaries such as bleach additives and“stain-stick” or pre-treat types, substrate-laden products such as dryeradded sheets, dry and wetted wipes and pads, nonwoven substrates, andsponges; as well as sprays and mists. All of such products which wereapplicable may be in standard, concentrated or even highly concentratedform even to the extent that such products may in certain aspect benon-aqueous.

As used herein, articles such as “a” and “an” when used in a claim, areunderstood to mean one or more of what is claimed or described.

As used herein, the terms “include”, “includes” and “including” aremeant to be non-limiting.

As used herein, the term “solid” includes granular, powder, bar andtablet product forms.

As used herein, the term “fluid” includes liquid, gel, paste and gasproduct forms.

As used herein, the term “situs” includes paper products, fabrics,garments, hard surfaces, hair and skin.

Unless otherwise noted, all component or composition levels are inreference to the active portion of that component or composition, andare exclusive of impurities, for example, residual solvents orby-products, which may be present in commercially available sources ofsuch components or compositions.

All percentages and ratios are calculated by weight unless otherwiseindicated. All percentages and ratios are calculated based on the totalcomposition unless otherwise indicated.

It should be understood that every maximum numerical limitation giventhroughout this specification includes every lower numerical limitation,as if such lower numerical limitations were expressly written herein.Every minimum numerical limitation given throughout this specificationwill include every higher numerical limitation, as if such highernumerical limitations were expressly written herein. Every numericalrange given throughout this specification will include every narrowernumerical range that falls within such broader numerical range, as ifsuch narrower numerical ranges were all expressly written herein.

Suitable Perfume Raw Materials (Herein after “PRMs”)

Suitable PRMs include the PRMs listed in Table 1 below and stereoisomersthereof.

Chemical structure IUPAC Names Molecules Characteristics 1

2-cyclohexyl-1-phenylethanone Honey, pineapple, fruity, powerful(lingers) 2

2-methyl-4-phenyloctan-3-one Spicy, Celery, green, basil 3

2,5-dimethyl-4-phenylhexan-3-one Honey, tea, aromatic, hay 4

2-methyl-4-phenylhexan-3-one Rose, friuty 5

2-cyclohexyl-1-(4- methylphenyl)ethanone 2-cyclohexyl-1-p-tolylethanoneFloral, petrol/rubbery (styrene) 6

2-cycloheptyl-1-phenylethanone Almond, sweet, anisic, spicy 7

2-cyclopentyl-1-p-tolylethanone sweet, fruity (almond), floral(rose-geranium) 8

2-cyclopentyl-1-(4- ethylphenyl)ethanone musty, cheesy 9

2-cyclopentyl-1-(2,4,6- trimethylphenyl)ethanone clean nice character 10

2-cyclopentyl-1-phenylethanone cheesy, rose, floral, fruity ester,pineapple, acidic 11

3-cyclohexyl-1-phenylpropan-1-one Almond, floral, fruity (apple) 12

3-cyclohexyl-1-(4- ethylphenyl)propan-1-one Animalic, Matallic 13

3-cyclohexyl-1-(4- methylphenyl)propan-1-one3-clohexyl-1-p-tolylpropan-1-one jasmin, ylang, animalic note 14

3-cyclohexyl-1-(2,4,6- trimethylphenyl)propan-1-one floral (muguet),green, fresh, sweet 15

4-(4-methylcyclohex-3-enyl)pentan- 2-ol Green, citrus, hay, cut grass 16

5-(4-methylcyclohex-3-enyl)hexan-3- ol Citrus, aldehydic, floral,muguet, unique in character 17

2-methyl-4-(4-methylcyclohex-3- enyl)pentan-2-ol Citrus, root, camphor18

6-(4-methylcyclohex-3-enyl)hept-1- en-4-ol Geranium, floral 19

2-methyl-5-(4-methylcyclohex-3- enyl)hexan-3-ol Aldehydic, citrus, spicy20

2,2-dimethyl-5-(4-methylcyclohex-3- enyl)hexan-3-ol Fruity (apple),diffusive, floral 21

2-(4-mcthylcyclohex-3-enyl)nonan-4- one Woody, cedar 22

4-(4-methylcyclohex-3-enyl)pentan- 2-one Fruity, Vertenex (woody), sournote, acrylic, very diffusive 23

5-(4-methylcyclohex-3-enyl)hexan-3- one Smokey, oily/buttery, ozonic,sour 24

2-methyl-5-(4-methylcyclohex-3- enyl)hexan-3-one Jasmin, lactonic,floral 25

2-(4-methylcyclohex-3-enyl)heptan- 4-one Floral, lactonic 26

6-(4-methylcyclohex-3-enyl)hept-1- en-4-one Fatty, aldehydic, frutene 27

2,2-dimethyl-5-(4-methylcyclohex-3- enyl)hexan-3-one Herbal, Tea,Terpentine 28

2,2-dimethyl-5-(4-methylcyclohex-3- enyl)hexan-3-yl acetate Floral,fruity 29

5-(4-methylcyclohex-3-enyl)hexan-3- yl acetate Fruity, Cassis 30

3-methyl-4-phenylbut-3-en-2-one floral (rose), citris, nitrilic, verydiffusive 31

4-(4-methylphenyl)butan-2-one, 4-p-tolylbutan-2-one Floral, Sweet,Anisic 32

1-(3-methylphenyl)pent-1-en-3-one 1-m-tolylpent-1-en-3-one Chlorinated(bleach), honey, almond 33

3-methyl-4-(4-methylphenyl)but-3- en-2-one3-methyl-4-p-tolylbut-3-en-2-one buttery 34

4-(2-methyl-3-oxobut-1- enyl)benzonitrile Sweet (honey), fruity 35

1-phenylhex-1-en-3-one Almond, sweet, candy 36

1-(2-methylphenyl)pent-1-en-3-one 1-o-tolylpent-1-en-3-one Floral,fruity, almond, saffron, anisic, diffusive 37

3-methyl-4-(2-methylphenyl)but-3- en-2-one3-methyl-4-o-tolylbut-3-en-2-one rose, buttery, ionone 38

3-methyl-4-(3-methylphenyl)but-3- en-2-one3-methyl-4-m-tolylbut-3-en-2-one nice, sweet, caramel, nutty 39

4-(4-methoxyphenyl)-3-methylbut-3- en-2-one sweet, burnt caramel 40

3-(4-methylbenzylidene)pentan-2-one floral, mimosa 41

1-(2-methylphenyl)hex-1-en-3-one 1-o-tolylhex-1-en-3-one Sweet, anisic,almond 42

1-(2,4,6-trimethylphenyl)hex-1-en-3- one Spicy, violet, rosy 43

1-(2,4,6-trimethylphenyl)pent-1-en-3- one Saffron, floral, animalic 44

3-methyl-4-(2,4,6- trimethylphenyl)but-3-en-2-one Aromatic, herbal,anisic 45

1-(2,6-dimethylphenyl)hex-1-en-3- one Floral, violet 46

1-(2,6-dimethylphenyl)pent-1-en-3- one Spicy, floral, saffron 47

1-(3-methylphenyl)hex-1-en-3-one 1-m-tolylhex-1-en-3-one Sweet, fruity,almond 48

1-cyclohexyl-2-phenylpropan-1-one Glue, rose, fruity 49

2,2,4,7-tetramethyloct-6-en-3-one citrus, herbal (lavender ketone hint)50

2,4(R,S),7-trimethyloct-6-en-3-one grapefruit, green 51

2,2,4,4,7-pentamethyloct-6-en-3-one lime, spicy, herbal, diffusive,citrus, citronella 52

Ethyl 2(R,S),5-dimethyl-2- (pivaloyl)hex-4-enoate 53

2,2,7-Trimethyl-4-(3-methylbut-2- enyl)oct-6-en-3-one 54

1-(1-(3-methylbut-2- enyl)cyclohexyl)ethanone rose, citrus, grapefruit55

1-(1-(3-methylbut-2- enyl)cyclohexyl)propan-1-one chemical 56

2-methyl-1-(1-(3-methylbut-2- enyl)cyclohexyl)propan-1-one weak (gunpowder) 57

4,4,7-trimethyloct-6-en-3-one rosey-geranium, grapefruit 58

1-(1-(3-methylbut-2- enyl)cyclopentyl)ethanone Grapefruit 59

1-(1-(3-methylbut-2- enyl)cyclopentyl)propan-1-one rose, fruity 60

3,6-dimethyl-3-(3-methylbut-2- enyl)hept-5-en-2-one Rose 61

3(R,S),6-dimethylhept-5-en-2-one 62

1-(1-(3-hydroxy-3- methylbutyl)cyclohexyl)-2- methylpropan-1-onechemical, acid 63

5-methyl-2(R,S)-(prop-1-en-2-yl)- hex-4-enoic acid 64

2-methyl-1-(1-(3-methylbut-2- enyl)cyclopentyl)propan-1-one fruity,chemical 65

4,7-dimethyl-4-(3-methylbut-2- enyl)oct-6-en-3-one Rose 66

2,4,7-trimethyl-4-(3-methylbut-2- enyl)oct-6-en-3-one Bleach 67

3(R,S),5,5,8-tetramethylnon-7-en-4- one fruity, grapefruit 68

1-(1-(3-methylbut-2- enyl)cyclopropyl)ethanone Fruity, ethereal 69

2-methyl-1-(1-(3-(R,S)-methylbut-2- enyl)cyclopropyl)butan-1-one fruity(grapefruit-plum) 70

2-methyl-1-(1-(3-methylbut-2- enyl)cyclopropyl)propan-1-one citrus,grapefruit 71

1-(1-(3-methylbut-2- enyl)cyclopropyl)pentan-1-one fruity-spicy(garpaccio)- metallic 72

9-methyldec-8-en-3 one waxy, fruity, clean (--> green, violet) 73

2,5-dimethyl-2-(3-methylbut-2- enyl)hex-4-enenitrile geranium, rose,terpenic 74

1-(3-methylbut-2- enyl)cyclopentanecarbonitrile spicy, nutty, rubbery 75

1-(3-methylbut-2- enyl)cyclohexanecarbonitrile herbal-aromatic,floral-green 76

1-(3-methylbut-2- enyl)cyclopropanecarbonitrile minty, nutty 77

1-(3-methylbut-2- enyl)cyclobutanecarbonitrile celery, diffusive 78

2-methyl-1-(1-(3-(R,S)-methylbut-2- enyl)cyclobutyl)butan-1-one fruity,herbal (menthol) 79

1-(1-(3-methylbut-2- enyl)cyclobutyl)ethanone citrus, aromatic,diffusive 80

2-(R,S)-methyl-1-(1- phenylcyclopropyl)butan-1-one woody, earthy 81

1-(1-(3-methylbut-2- enyl)cyclobutyl)pentan-1-one Spearmint 82

2-methyl-1-(1-(3-methylbut-2- enyl)cyclobutyl)propan-1-one pine,terpenic 83

1-(1-phenylcyclopropyl)propan-1-one woody, earthy, orange (over- ripe),84

2-methyl-1-(1- phenylcyclopropyl)propan-1-one woody, gunpowder,(fougere) 85

1-(1-(3-methylbut-2- enyl)cyclopropyl)propan-1-one terpenic, herbal 86

3-methyl-1-(1-(3-methylbut-2- enyl)cyclopropyl)butan-1-one metallic,fruity 87

1-(1-p-tolylcyclopropyl)propan-1-one oily, solventy, nutty 88

2-(R,S)-methyl-1-(1-p- tolylcyclopropyl)butan-1-one woody, weak 89

1-(1-(3-methylbut-2-enyl)-3- methylenecyclobutyl)ethanone herbal(edible-oxo) 90

1-(1-phenylcyclobutyl)pentan-1-one styrene, oily 91

2,2,5-trimethylhex-4-enenitrile earthy, ozonic, vetyver 92

6,6,9-trimethyldec-8-en-5-one floral, intense 93

2,5,5,8-tetramethylnon-7-en-4-one floral, valerianic 94

1-(1-(3-methylbut-2- enyl)cyclopcntyl)pentan-1-one floral, valerianic 95

3-methyl-1-(1-(3-methylbut-2- enyl)cyclopentyl)butan-1-one floral,valerianic 96

2,2-dimethyl-1-(1-(3-methylbut-2- enyl)cyclopropyl)propan-1-one citrus,fresh, diffusive 97

2-methyl-1-(1-p- tolylcyclopropyl)propan-1-one almond, chemical 98

1-(1-((E)-3,7-dimethylocta-2,6- dienyl)cyclopropyl)ethanone Spicy 99

2-methyl-1-(1-((E)-3,7-dimethylocta- 2,6-dienyl)cyclopropyl)butan-1-oneherbal, green, fruity (natural) 100

2,4-dimethyl-2-m-tolylpentan-3-one intense, tobacco (sweet), earthy 101

2-methyl-2-m-tolylpropanetrile intense, root, vetyver 102

3-methyl-3-m-tolylbutan-2-one burnt, caramelized 103

2-methyl-2-m-tolylpentan-3-one diffusive, orange flower 104

1-(1-p-tolylcyclopentyl)ethanone spicy, vegetable 105

7-methyl-1-phenyloct-6-en-1-one truffle, oriental bouillon 106

2,2-dimethyl-3-o-tolylpropanenitrile saffras, earthy, woody 107

3,3-dimethyl-4-o-tolylbutan-2-one Cedarwood 108

2,2-dimethyl-1-o-tolylpentan-3-one woody, citrus, medicinal 109

o-methyl- benzylcyclopropanecarbonitrile woody, spicy, chemical 110

2,2,4-trimethyl-1-o-tolylhexan-3-one floral, terpineol, camomile, green111

1-(1-(2-methylbenzyl)- cyclopropyl)propanone rose, violet, woody 112

1-(1-(2- methylbenzyl)cyclopropyl)ethanone leathery, powdery 113

2-(R,S)-methyl-1-(1-(2- methylbenzyl)cyclopropyl)butan-1- one fruity,tutti-frutti, citrus 114

2-methyl-1-(1-(2- methylbenzyl)cyclopropyl)propan-1- one citrus, fruity(apple) 115

2,2,5-trimethyl-1-phenylhexan-3-one intense, woody, celery, anima 116

2-(1-(3-methylbut-2- enyl)cyclopropyl)propan-2-ol intense, floral,lilac, terpineol 117

1-(1-(3-methylbut-2- enyl)cyclopbutyl)propan-1-one woody, camphor,costus 118

2-(R,S)-(1-(3-methylbut-2- enyl)cyclobutyl)butan-2-ol citrus, herbal,bleach 119

1-(R,S)-(1-(3-methylbut-2- enyl)cyclobutyl)propan-1-ol Weak 120

9-methyldec-1,8-dien-3-one diffusive, very intense, metallic, smoky (gunpowder) 121

2,2-dimethyl-3-(R,S)- phenylbutanenitrile tobacco, floral (violet) 122

4,4-dimethyl-5-(R,S)-phenylhexan-3- one herbal (green, chamomile) 123

1-cyclopentyl-7-methyloct-6-en-1- one very intense, nutty, spicy, green(galbanum) 124

2,2-dimethyl-3-p-tolylpropanenitrile chervil, fennel, celery, mint 125

3-(4-methoxy-3-methylphenyl)-3- methylbutan-2-one leatherym, quinone 126

2,2,4-(R,S)-trimethyl-1-p-tolylhexan- 3-one weak, chocolate, nutty 127

3,3-dimethyl-4-(R,S)-phenylpentan- 2-one diffusive, herbal, citrus 128

2,2-dimethyl-1-p-tolylpentan-3-one fennel, herbal 129

3-(R,S)-(1-(3-methylbut-2- enyl)cyclobutyl)heptan-3-ol citrus, amber 130

3-cyclohexyl-2,2- dimethylpropanenitrile intense, mint, marine, spicy131

1-cyclohexyl-2,2,4-trimethylpentan- 3-one Peppery 132

1-(R,S)-(1-phenylethyl)- cyclobutanecarbonitrile chemical, solventy 133

1-(1-(R,S)-(1-phenylethyl)- cyclobutyl)ethanone chemical, solventy,animalic 134

2-methyl-1-(1-(R,S)-(1- phenylethyl)cyclobutyl)propan-1-one chemical,orange flower 135

2-methyl-1-(R,S)-(1-(1-(R,s)- phenylethyl)cyclobutyl)propan-1-olChemical 136

1-(1-(R,S)- phenylethyl)cyclopropanecarbonitrile Petrol 137

1-(1-(1-(R,S)- phenylethyl)cyclopropyl)ethanone green, floral, chemical138

2,2-dimethyl-3-m-tolylpropanenitrile orange crystals 139

3-(4-tert-butylphcnyl)-2,2- dimethylpropanenitrile woody, floral 140

1-(1-phenylcyclopropyl)but-3-en-1- one fruity (berries), green 141

1-(1-phenylcyclopropyl)but-3-en-1- (R,s)-ol floral, chemical 142

4-(4-tert-butylphenyl)-3,3- dimethylbutan-2-one Sulphuric 143

2,2-dimethyl-4-phenylbutanenitrile Chemical 144

11-methyldodec-10-en-5-one Seafood 145

2,9-dimethyldec-8-en-3-one intense, fruity, oily, clean 146

2,10-dimethylundec-9-en-4-one intense, waxy, aldehydic, floral, fruity(melon) 147

2,2,9-trimethyldec-8-en-3-one intense, woody, waxy 148

2,2,3-(R,S),7-tetramethyloct-6- enenitrile citrus, waxy, bleach 149

4,4,5-(R,S),9-tetramethyldec-8-en-3- one intense, floral, waxy 150

6,6,7-(R,S),11-tetramethyldodec-10- en-5-one celery, green, floral 151

3,3-dimethyl-5-phenylpentan-s-one glue, sweet 152

2-((R,S)-cyclohex-2-enyl)-2- methylpropanenitrile intense, woody,camphoraceous 153

2-((R,S)-cyclohex-2-enyl)-2,5- dimethylhexan-3-one citrus, herbal 154

3,3-dimethyl-1-phenyloctan-4-one Chemical 155

2-((R,S)-cyclohex-2-enyl)-2- methylpentan-3-one intense, fruity, floral,woody, spicy 156

4,4-dimethyl-6-phenylhexan-3-one Floral, woody 157

2,2-dimethyl-5-phenylpentanenitrile citrus, nitrile, chemical, clean 158

2,2-dimethylhept-6-enenitrile intense, floral, celery 159

6,6-dimethylundec-10-en-5-one Waxy, clean 160

3,3-dimethyl-6-phenylhexan-2-one citrus, herbal 161

2,2-dimethyl-4-((1R,5S)-6,6- dimethylbicyclo[3.1.1]hept-2-en-2-yl)butanenitrile floral, spicy (peppery), woody

The PRMs disclosed in Table 1 above may provide one or more of thefollowing benefits at a level that Applicants believe is unexpected inview of PRMs in general: neat product odor; wet fabric odor when appliedto a fabric; dry fabric odor when applied to a fabric; reduced leakagefrom an encapsulate, including an encapsulate such as a perfumemicrocapsule; increased head space versus neat oil in certain perfumedelivery technologies; odor when used in a matrix perfume delivery thatis applied to a package; neat product odor when applied to a cleaningand/or treatment composition; fine fragrance composition odor when usedin a fine fragrance; dry hair odor when a composition comprising such aPRM is applied to hair; PRM bloom from a solution comprising such a PRMand new PRM character when applied to a situs. Confirmation of suchbenefits can be obtained by applying standard test methodologies.

The PRMs and stereoisomers of such PRMs (also known as molecules in theexamples of the present specification) disclosed in Table 1 above can bemade in accordance with the respective teachings found, for example inthe examples of the present specification.

In one aspect, a PRM having the structure of Table 1 PRM 16, 20, 27, 28,118, 123 and 140 are disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereofare suitable for use, as defined by the present specification, inconsumer products at levels, based on total consumer product weight offrom about 0.0001% to about 25%, from about 0.0005% to about 10%, fromabout 0.001% to about 5%, from about 0.005% to about 2.5%, or even from0.01% to about 1%. Such PRMs and stereoisomers thereof may be used incombination in the aforementioned consumer product. In one aspect, aconsumer product that may comprise one or more PRMs selected from Table1 PRMs 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 118, 123,140 and stereoisomers of such PRMs is disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereofare suitable for use, as defined by the present specification, incleaning and/or treatment composition at levels, based on total cleaningand treatment products weight of from about 0.0001% to about 25%, fromabout 0.0005% to about 10%, from about 0.001% to about 5%, from about0.005% to about 2.5%, or even from 0.01% to about 1%. Such PRMs andstereoisomers thereof may be used in combination in the aforementionedcleaning and/treatment compositions. In one aspect, a cleaning and/ortreatment composition that may comprise one or more PRMs selected fromTable 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18,19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 77, 100, 101, 107, 108, 110,117, 118, 123, 127, 140 and stereoisomers of such PRMs is disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereofare suitable for use, as defined by the present specification, in fabricand/or hard surface cleaning and/or treatment compositions at levels,based on total fabric and/or hard surface cleaning and/or treatmentcomposition weight of from about 0.00001% to about 25%, from 0.00005% toabout 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, or evenfrom 0.001% to about 0.5%. Such PRMs and stereoisomers thereof may beused in combination in the aforementioned fabric and/or hard surfacecleaning and/or treatment compositions. In one aspect, a fabric and/orhard surface cleaning and/or treatment composition that may comprise oneor more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10,11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29,33, 34, 35, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 50, 51, 52,53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70,71, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 93,94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108,109, 110, 111, 112, 113, 114, 115, 117, 118, 119, 121, 122, 123, 124,125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138,139, 140, 141, 142, 143, 144, 145, 146, 147, 149, 150, 151, 152, 153,154, 155, 156, 157, 158, 159, 160, 161 and stereoisomers of such PRMs isdisclosed.

In one aspect, a detergent that may comprise the same level of the PRMsas disclosed for the aforementioned fabric and hard surface cleaningand/or treatment compositions is disclosed. In one aspect, a detergentthat may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23,24, 25, 26, 27, 28, 29, 33, 34, 35, 37, 38, 39, 40, 41, 42, 43, 44, 45,46, 47, 48 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64,65, 66, 67, 68, 69, 70, 71, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85,86, 87, 88, 89, 90, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104,105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 117, 118, 119,121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134,135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 149,150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161 andstereoisomers of such PRMs is disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereofare suitable for use, in highly compacted consumer products, includinghighly compacted fabric and hard surface cleaning and/or treatmentcompositions, for example highly compacted detergents that may be solidsor fluids, at levels, based on total composition weight, of from about0.00001% to about 25%, from 0.00005% to about 10%, from 0.0001% to about5%, from 0.0005% to about 1.0%, or even from 0.001% to about 0.5%. SuchPRMs and stereoisomers thereof may be used in combination in theaforementioned highly compacted detergent compositions. Such highlycompact detergents typically comprise a higher than normal percentage ofactive ingredients. In one aspect, a highly compacted detergent that maycomprise one or more PRMs selected from Table 1 PRMs and stereoisomersof such PRMs is disclosed. In another aspect, highly compacted adetergent that may comprise one or more PRMs selected from Table 1 PRMs1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38,39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56,57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74,75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92,93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108,109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122,123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136,137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150,151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161 and stereoisomersof such PRMs is disclosed.

Perfume Delivery Systems

Certain perfume delivery systems, methods of making certain perfumedelivery systems and the uses of such perfume delivery systems aredisclosed in USPA 2007/0275866 A1. Such perfume delivery systemsinclude:

I. Polymer Assisted Delivery (PAD):

This perfume delivery technology uses polymeric materials to deliverperfume materials. Classical coacervation, water soluble or partlysoluble to insoluble charged or neutral polymers, liquid crystals, hotmelts, hydrogels, perfumed plastics, microcapsules, nano- andmicro-latexes, polymeric film formers, and polymeric absorbents,polymeric adsorbents, etc. are some examples. PAD includes but is notlimited to:

-   -   a.) Matrix Systems: The fragrance is dissolved or dispersed in a        polymer matrix or particle. Perfumes, for example, may be 1)        dispersed into the polymer prior to formulating into the product        or 2) added separately from the polymer during or after        formulation of the product. Diffusion of perfume from the        polymer is a common trigger that allows or increases the rate of        perfume release from a polymeric matrix system that is deposited        or applied to the desired surface (situs), although many other        triggers are know that may control perfume release. Absorption        and/or adsorption into or onto polymeric particles, films,        solutions, and the like are aspects of this technology. Nano- or        micro-particles composed of organic materials (e.g., latexes)        are examples. Suitable particles include a wide range of        materials including, but not limited to polyacetal,        polyacrylate, polyacrylic, polyacrylonitrile, polyamide,        polyaryletherketone, polybutadiene, polybutylene, polybutylene        terephthalate, polychloroprene, poly ethylene, polyethylene        terephthalate, polycyclohexylene dimethylene terephthalate,        polycarbonate, polychloroprene, polyhydroxyalkanoate,        polyketone, polyester, polyethylene, polyetherimide,        polyethersulfone, polyethylenechlorinates, polyimide,        polyisoprene, polylactic acid, polymethylpentene, polyphenylene        oxide, polyphenylene sulfide, polyphthalamide, polypropylene,        polystyrene, polysulfone, polyvinyl acetate, polyvinyl chloride,        as well as polymers or copolymers based on        acrylonitrile-butadiene, cellulose acetate, ethylene-vinyl        acetate, ethylene vinyl alcohol, styrene-butadiene, vinyl        acetate-ethylene, and mixtures thereof.        -   “Standard” systems refer to those that are “pre-loaded” with            the intent of keeping the pre-loaded perfume associated with            the polymer until the moment or moments of perfume release.            Such polymers may also suppress the neat product odor and            provide a bloom and/or longevity benefit depending on the            rate of perfume release. One challenge with such systems is            to achieve the ideal balance between 1) in-product stability            (keeping perfume inside carrier until you need it) and 2)            timely release (during use or from dry situs). Achieving            such stability is particularly important during in-product            storage and product aging. This challenge is particularly            apparent for aqueous-based, surfactant-containing products,            such as heavy duty liquid laundry detergents. Many            “Standard” matrix systems available effectively become            “Equilibrium” systems when formulated into aqueous-based            products. One may select an “Equilibrium” system or a            Reservoir system, which has acceptable in-product diffusion            stability and available triggers for release (e.g.,            friction). “Equilibrium” systems are those in which the            perfume and polymer may be added separately to the product,            and the equilibrium interaction between perfume and polymer            leads to a benefit at one or more consumer touch points            (versus a free perfume control that has no polymer-assisted            delivery technology). The polymer may also be pre-loaded            with perfume; however, part or all of the perfume may            diffuse during in-product storage reaching an equilibrium            that includes having desired perfume raw materials (PRMs)            associated with the polymer. The polymer then carries the            perfume to the surface, and release is typically via perfume            diffusion. The use of such equilibrium system polymers has            the potential to decrease the neat product odor intensity of            the neat product (usually more so in the case of pre-loaded            standard system). Deposition of such polymers may serve to            “flatten” the release profile and provide increased            longevity. As indicated above, such longevity would be            achieved by suppressing the initial intensity and may enable            the formulator to use more high impact or low odor detection            threshold (ODT) or low Kovats Index (KI) PRMs to achieve            FMOT benefits without initial intensity that is too strong            or distorted. It is important that perfume release occurs            within the time frame of the application to impact the            desired consumer touch point or touch points. Suitable            micro-particles and micro-latexes as well as methods of            making same may be found in USPA 2005/0003980 A1. Matrix            systems also include hot melt adhesives and perfume            plastics. In addition, hydrophobically modified            polysaccharides may be formulated into the perfumed product            to increase perfume deposition and/or modify perfume            release. All such matrix systems, including for example            polysaccarides and nanolatexes may be combined with other            PDTs, including other PAD systems such as PAD reservoir            systems in the form of a perfume microcapsule (PMC). Polymer            Assisted Delivery (PAD) matrix systems may include those            described in the following references: US Patent            Applications 2004/0110648 A1; 2004/0092414 A1; 2004/0091445            A1 and 2004/0087476 A1; and U.S. Pat. Nos. 6,531,444;            6,024,943; 6,042,792; 6,051,540; 4,540,721 and 4,973,422.        -   Silicones are also examples of polymers that may be used as            PDT, and can provide perfume benefits in a manner similar to            the polymer-assisted delivery “matrix system”. Such a PDT is            referred to as silicone-assisted delivery (SAD). One may            pre-load silicones with perfume, or use them as an            equilibrium system as described for PAD. Suitable silicones            as well as making same may be found in WO 2005/102261; USPA            20050124530A1; USPA 20050143282A1; and WO 2003/015736.            Functionalized silicones may also be used as described in            USPA 2006/003913 A1. Examples of silicones include            polydimethylsiloxane and polyalkyldimethylsiloxanes. Other            examples include those with amine functionality, which may            be used to provide benefits associated with amine-assisted            delivery (AAD) and/or polymer-assisted delivery (PAD) and/or            amine-reaction products (ARP). Other such examples may be            found in U.S. Pat. No. 4,911,852; USPA 2004/0058845 A1; USPA            2004/0092425 A1 and USPA 2005/0003980 A1.    -   b.) Reservoir Systems: Reservoir systems are also known as a        core-shell type technology, or one in which the fragrance is        surrounded by a perfume release controlling membrane, which may        serve as a protective shell. The material inside the        microcapsule is referred to as the core, internal phase, or        fill, whereas the wall is sometimes called a shell, coating, or        membrane. Microparticles or pressure sensitive capsules or        microcapsules are examples of this technology. Microcapsules of        the current invention are formed by a variety of procedures that        include, but are not limited to, coating, extrusion,        spray-drying, interfacial, in-situ and matrix polymerization.        The possible shell materials vary widely in their stability        toward water. Among the most stable are polyoxymethyleneurea        (PMU)-based materials, which may hold certain PRMs for even long        periods of time in aqueous solution (or product). Such systems        include but are not limited to urea-formaldehyde and/or        melamine-formaldehyde. Gelatin-based microcapsules may be        prepared so that they dissolve quickly or slowly in water,        depending for example on the degree of cross-linking. Many other        capsule wall materials are available and vary in the degree of        perfume diffusion stability observed. Without wishing to be        bound by theory, the rate of release of perfume from a capsule,        for example, once deposited on a surface is typically in reverse        order of in-product perfume diffusion stability. As such,        urea-formaldehyde and melamine-formaldehyde microcapsules for        example, typically require a release mechanism other than, or in        addition to, diffusion for release, such as mechanical force        (e.g., friction, pressure, shear stress) that serves to break        the capsule and increase the rate of perfume (fragrance)        release. Other triggers include melting, dissolution, hydrolysis        or other chemical reaction, electromagnetic radiation, and the        like. The use of pre-loaded microcapsules requires the proper        ratio of in-product stability and in-use and/or on-surface        (on-situs) release, as well as proper selection of PRMs.        Microcapsules that are based on urea-formaldehyde and/or        melamine-formaldehyde are relatively stable, especially in near        neutral aqueous-based solutions. These materials may require a        friction trigger which may not be applicable to all product        applications. Other microcapsule materials (e.g., gelatin) may        be unstable in aqueous-based products and may even provide        reduced benefit (versus free perfume control) when in-product        aged. Scratch and sniff technologies are yet another example of        PAD. Perfume microcapsules (PMC) may include those described in        the following references: US Patent Applications: 2003/0125222        A1; 2003/215417 A1; 2003/216488 A1; 2003/158344 A1; 2003/165692        A1; 2004/071742 A1; 2004/071746 A1; 2004/072719 A1; 2004/072720        A1; 2006/0039934 A1; 2003/203829 A1; 2003/195133 A1; 2004/087477        A1; 2004/0106536 A1; and U.S. Pat. Nos. 6,645,479 B1; 6,200,949        B1; 4,882,220; 4,917,920; 4,514,461; 6,106,875 and 4,234,627,        3,594,328 and U.S. RE 32713.        II. Molecule-Assisted Delivery (MAD):

Non-polymer materials or molecules may also serve to improve thedelivery of perfume. Without wishing to be bound by theory, perfume maynon-covalently interact with organic materials, resulting in altereddeposition and/or release. Non-limiting examples of such organicmaterials include but are not limited to hydrophobic materials such asorganic oils, waxes, mineral oils, petrolatum, fatty acids or esters,sugars, surfactants, liposomes and even other perfume raw material(perfume oils), as well as natural oils, including body and/or othersoils. Perfume fixatives are yet another example. In one aspect,non-polymeric materials or molecules have a CLogP greater than about 2.Molecule-Assisted Delivery (MAD) may also include those described inU.S. Pat. No. 7,119,060 and U.S. Pat. No. 5,506,201.

III. Fiber-Assisted Delivery (FAD):

The choice or use of a situs itself may serve to improve the delivery ofperfume. In fact, the situs itself may be a perfume delivery technology.For example, different fabric types such as cotton or polyester willhave different properties with respect to ability to attract and/orretain and/or release perfume. The amount of perfume deposited on or infibers may be altered by the choice of fiber, and also by the history ortreatment of the fiber, as well as by any fiber coatings or treatments.Fibers may be woven and non-woven as well as natural or synthetic.Natural fibers include those produced by plants, animals, and geologicalprocesses, and include but are not limited to cellulose materials suchas cotton, linen, hemp jute, flax, ramie, and sisal, and fibers used tomanufacture paper and cloth. Fiber-Assisted Delivery may consist of theuse of wood fiber, such as thermomechanical pulp and bleached orunbleached kraft or sulfite pulps. Animal fibers consist largely ofparticular proteins, such as silk, sinew, catgut and hair (includingwool). Polymer fibers based on synthetic chemicals include but are notlimited to polyamide nylon, PET or PBT polyester, phenol-formaldehyde(PF), polyvinyl alcohol fiber (PVOH), polyvinyl chloride fiber (PVC),polyolefins (PP and PE), and acrylic polymers. All such fibers may bepre-loaded with a perfume, and then added to a product that may or maynot contain free perfume and/or one or more perfume deliverytechnologies. In one aspect, the fibers may be added to a product priorto being loaded with a perfume, and then loaded with a perfume by addinga perfume that may diffuse into the fiber, to the product. Withoutwishing to be bound by theory, the perfume may absorb onto or beadsorbed into the fiber, for example, during product storage, and thenbe released at one or more moments of truth or consumer touch points.

IV. Amine Assisted Delivery (AAD):

The amine-assisted delivery technology approach utilizes materials thatcontain an amine group to increase perfume deposition or modify perfumerelease during product use. There is no requirement in this approach topre-complex or pre-react the perfume raw material(s) and amine prior toaddition to the product. In one aspect, amine-containing AAD materialssuitable for use herein may be non-aromatic; for example,polyalkylimine, such as polyethyleneimine (PEI), or polyvinylamine(PVAm), or aromatic, for example, anthranilates. Such materials may alsobe polymeric or non-polymeric. In one aspect, such materials contain atleast one primary amine. This technology will allow increased longevityand controlled release also of low ODT perfume notes (e.g., aldehydes,ketones, enones) via amine functionality, and delivery of other PRMs,without being bound by theory, via polymer-assisted delivery forpolymeric amines. Without technology, volatile top notes can be lost tooquickly, leaving a higher ratio of middle and base notes to top notes.The use of a polymeric amine allows higher levels of top notes and otherPRMS to be used to obtain freshness longevity without causing neatproduct odor to be more intense than desired, or allows top notes andother PRMs to be used more efficiently. In one aspect, AAD systems areeffective at delivering PRMs at pH greater than about neutral. Withoutwishing to be bound by theory, conditions in which more of the amines ofthe AAD system are deprotonated may result in an increased affinity ofthe deprotonated amines for PRMs such as aldehydes and ketones,including unsaturated ketones and enones such as damascone. In anotheraspect, polymeric amines are effective at delivering PRMs at pH lessthan about neutral. Without wishing to be bound by theory, conditions inwhich more of the amines of the AAD system are protonated may result ina decreased affinity of the protonated amines for PRMs such as aldehydesand ketones, and a strong affinity of the polymer framework for a broadrange of PRMs. In such an aspect, polymer-assisted delivery may bedelivering more of the perfume benefit; such systems are a subspecies ofAAD and may be referred to as Amine-Polymer-Assisted Delivery or APAD.In some cases when the APAD is employed in a composition that has a pHof less than seven, such APAD systems may also be consideredPolymer-Assisted Delivery (PAD). In yet another aspect, AAD and PADsystems may interact with other materials, such as anionic surfactantsor polymers to form coacervate and/or coacervates-like systems. Inanother aspect, a material that contains a heteroatom other thannitrogen, for example sulfur, phosphorus or selenium, may be used as analternative to amine compounds. In yet another aspect, theaforementioned alternative compounds can be used in combination withamine compounds. In yet another aspect, a single molecule may comprisean amine moiety and one or more of the alternative heteroatom moieties,for example, thiols, phosphines and selenols. Suitable AAD systems aswell as methods of making same may be found in US Patent Applications2005/0003980 A1; 2003/0199422 A1; 2003/0036489 A1; 2004/0220074 A1 andU.S. Pat. No. 6,103,678.

V. Cyclodextrin Delivery System (CD):

This technology approach uses a cyclic oligosaccharide or cyclodextrinto improve the delivery of perfume. Typically a perfume and cyclodextrin(CD) complex is formed. Such complexes may be preformed, formed in-situ,or formed on or in the situs. Without wishing to be bound by theory,loss of water may serve to shift the equilibrium toward the CD-Perfumecomplex, especially if other adjunct ingredients (e.g., surfactant) arenot present at high concentration to compete with the perfume for thecyclodextrin cavity. A bloom benefit may be achieved if water exposureor an increase in moisture content occurs at a later time point. Inaddition, cyclodextrin allows the perfume formulator increasedflexibility in selection of PRMs. Cyclodextrin may be pre-loaded withperfume or added separately from perfume to obtain the desired perfumestability, deposition or release benefit. Suitable CDs as well asmethods of making same may be found in USPA 2005/0003980 A1 and2006/0263313 A1 and U.S. Pat. Nos. 5,552,378; 3,812,011; 4,317,881;4,418,144 and 4,378,923.

VI. Starch Encapsulated Accord (SEA):

The use of a starch encapsulated accord (SEA) technology allows one tomodify the properties of the perfume, for example, by converting aliquid perfume into a solid by adding ingredients such as starch. Thebenefit includes increased perfume retention during product storage,especially under non-aqueous conditions. Upon exposure to moisture, aperfume bloom may be triggered. Benefits at other moments of truth mayalso be achieved because the starch allows the product formulator toselect PRMs or PRM concentrations that normally cannot be used withoutthe presence of SEA. Another technology example includes the use ofother organic and inorganic materials, such as silica to convert perfumefrom liquid to solid. Suitable SEAs as well as methods of making samemay be found in USPA 2005/0003980 A1 and U.S. Pat. No. 6,458,754 B1.

VII. Inorganic Carrier Delivery System (ZIC):

This technology relates to the use of porous zeolites or other inorganicmaterials to deliver perfumes. Perfume-loaded zeolite may be used withor without adjunct ingredients used for example to coat theperfume-loaded zeolite (PLZ) to change its perfume release propertiesduring product storage or during use or from the dry situs. Suitablezeolite and inorganic carriers as well as methods of making same may befound in USPA 2005/0003980 A1 and U.S. Pat. Nos. 5,858,959; 6,245,732B1; 6,048,830 and 4,539,135. Silica is another form of ZIC. Anotherexample of a suitable inorganic carrier includes inorganic tubules,where the perfume or other active material is contained within the lumenof the nano- or micro-tubules. In one aspect, the perfume-loadedinorganic tubule (or Perfume-Loaded Tubule or PLT) is a mineral nano- ormicro-tubule, such as halloysite or mixtures of halloysite with otherinorganic materials, including other clays. The PLT technology may alsocomprise additional ingredients on the inside and/or outside of thetubule for the purpose of improving in-product diffusion stability,deposition on the desired situs or for controlling the release rate ofthe loaded perfume. Monomeric and/or polymeric materials, includingstarch encapsulation, may be used to coat, plug, cap, or otherwiseencapsulate the PLT. Suitable PLT systems as well as methods of makingsame may be found in U.S. Pat. No. 5,651,976.

VIII. Pro-Perfume (PP):

This technology refers to perfume technologies that result from thereaction of perfume materials with other substrates or chemicals to formmaterials that have a covalent bond between one or more PRMs and one ormore carriers. The PRM is converted into a new material called a pro-PRM(i.e., pro-perfume), which then may release the original PRM uponexposure to a trigger such as water or light. Pro-perfumes may provideenhanced perfume delivery properties such as increased perfumedeposition, longevity, stability, retention, and the like. Pro-perfumesinclude those that are monomeric (non-polymeric) or polymeric, and maybe pre-formed or may be formed in-situ under equilibrium conditions,such as those that may be present during in-product storage or on thewet or dry situs. Nonlimiting examples of pro-perfumes include Michaeladducts (e.g., beta-amino ketones), aromatic or non-aromatic imines(Schiff bases), oxazolidines, beta-keto esters, and orthoesters. Anotheraspect includes compounds comprising one or more beta-oxy or beta-thiocarbonyl moieties capable of releasing a PRM, for example, an alpha,beta-unsaturated ketone, aldehyde or carboxylic ester. The typicaltrigger for perfume release is exposure to water; although othertriggers may include enzymes, heat, light, pH change, autoxidation, ashift of equilibrium, change in concentration or ionic strength andothers. For aqueous-based products, light-triggered pro-perfumes areparticularly suited. Such photo-pro-perfumes (PPPs) include but are notlimited to those that release coumarin derivatives and perfumes and/orpro-perfumes upon being triggered. The released pro-perfume may releaseone or more PRMs by means of any of the above mentioned triggers. In oneaspect, the photo-pro-perfume releases a nitrogen-based pro-perfume whenexposed to a light and/or moisture trigger. In another aspect, thenitrogen-based pro-perfume, released from the photo-pro-perfume,releases one or more PRMs selected, for example, from aldehydes, ketones(including enones) and alcohols. In still another aspect, the PPPreleases a dihydroxy coumarin derivative. The light-triggeredpro-perfume may also be an ester that releases a coumarin derivative anda perfume alcohol. In one aspect the pro-perfume is a dimethoxybenzoinderivative as described in USPA 2006/0020459 A1. In another aspect thepro-perfume is a 3′,5′-dimethoxybenzoin (DMB) derivative that releasesan alcohol upon exposure to electromagnetic radiation. In yet anotheraspect, the pro-perfume releases one or more low ODT PRMs, includingtertiary alcohols such as linalool, tetrahydrolinalool, ordihydromyrcenol. Suitable pro-perfumes and methods of making same can befound in U.S. Pat. Nos. 7,018,978 B2; 6,987,084 B2; 6,956,013 B2;6,861,402 B1; 6,544,945 B1; 6,093,691; 6,277,796 B1; 6,165,953;6,316,397 B1; 6,437,150 B1; 6,479,682 B1; 6,096,918; 6,218,355 B1;6,133,228; 6,147,037; 7,109,153 B2; 7,071,151 B2; 6,987,084 B2;6,610,646 B2 and 5,958,870, as well as can be found in USPA 2005/0003980A1 and USPA 2006/0223726 A1.

-   -   a.) Amine Reaction Product (ARP): For purposes of the present        application, ARP is a subclass or species of PP. One may also        use “reactive” polymeric amines in which the amine functionality        is pre-reacted with one or more PRMs to form an amine reaction        product (ARP). Typically the reactive amines are primary and/or        secondary amines, and may be part of a polymer or a monomer        (non-polymer). Such ARPs may also be mixed with additional PRMs        to provide benefits of polymer-assisted delivery and/or        amine-assisted delivery. Nonlimiting examples of polymeric        amines include polymers based on polyalkylimines, such as        polyethyleneimine (PEI), or polyvinylamine (PVAm). Nonlimiting        examples of monomeric (non-polymeric) amines include        hydroxylamines, such as 2-aminoethanol and its alkyl substituted        derivatives, and aromatic amines such as anthranilates. The ARPs        may be premixed with perfume or added separately in leave-on or        rinse-off applications. In another aspect, a material that        contains a heteroatom other than nitrogen, for example oxygen,        sulfur, phosphorus or selenium, may be used as an alternative to        amine compounds. In yet another aspect, the aforementioned        alternative compounds can be used in combination with amine        compounds. In yet another aspect, a single molecule may comprise        an amine moiety and one or more of the alternative heteroatom        moieties, for example, thiols, phosphines and selenols. The        benefit may include improved delivery of perfume as well as        controlled perfume release. Suitable ARPs as well as methods of        making same can be found in USPA 2005/0003980 A1 and U.S. Pat.        No. 6,413,920 B1.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereofare suitable for use in perfume delivery systems at levels, based ontotal perfume delivery system weight, of from 0.001% to about 50%, from0.005% to 30%, from 0.01% to about 10%, from 0.025% to about 5%, or evenfrom 0.025% to about 1%.

In one aspect, the perfume delivery systems disclosed herein aresuitable for use in consumer products, cleaning and treatmentcompositions and fabric and hard surface cleaning and/or treatmentcompositions, detergents, and highly compacted consumer products,including highly compacted fabric and hard surface cleaning and/ortreatment compositions, for example highly compacted detergents that maybe solids or fluids, at levels, based on total consumer product weight,from about 0.001% to about 20%, from about 0.01% to about 10%, fromabout 0.05% to about 5%, from about 0.1% to about 0.5%.

In one aspect, the amount of Table 1 PRMs, based on the totalmicrocapsules and/or nanocapsules (Polymer Assisted Delivery (PAD)Reservoir System) weight, may be from about 0.1% to about 99%, from 25%to about 95%, from 30 to about 90%, from 45% to about 90%, from 65% toabout 90%. In one aspect, microcapsules and/or nanocapsules that maycomprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6,7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25,26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43,44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61,62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79,80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97,98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112,113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126,127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140,141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154,155, 156, 157, 158, 159, 160, 161; stereoisomers of Table 1 PRMs 1, 2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22,23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40,41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58,59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76,77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94,95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109,110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123,124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137,138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151,152, 153, 154, 155, 156, 157, 158, 159, 160, 161; and mixtures thereof.PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 21, 22, 23, 24, 25,26, 27, 30, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46,47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66,67, 68, 69, 70, 71, 72, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89,90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 107, 108,110, 111, 112, 113, 114, 115, 117, 120, 122, 123, 125, 126, 127, 128,131, 133, 134, 137, 140, 142, 144, 145, 146, 147, 149, 150, 151, 153,154, 155, 156, 159 and 160 are ketones. PRMs 15, 16, 17, 18, 19, 20,116, 118, 119, 129, 135 and 141 are alcohols. PRMs 28, 29 and 52 areesters. PRMs 34, 73, 74, 75, 76, 77, 91, 101, 106, 109, 121, 124, 130,132, 136, 138, 139, 143, 148, 152, 157, 158 and 161 are nitriles.

In one aspect, the amount of total perfume based on total weight ofstarch encapsulates and starch agglomerates (Starch Encapsulated Accord(SEA)) ranges from 0.1% to about 99%, from 25% to about 95%, from 30 toabout 90%, from 45% to about 90%, from 65% to about 90%. In one aspect,the PRMs disclosed in Table 1 and stereoisomers thereof are suitable foruse in such starch encapsulates and starch agglomerates. Such PRMs andstereoisomers thereof may be used in combination in such starchencapsulates and starch agglomerates.

In one aspect, the amount of total perfume based on total weight of[cyclodextrin-perfume] complexes (Cyclodextrin (CD)) ranges from 0.1% toabout 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% toabout 50%, from 5% to about 25%. In one aspect, the PRMs disclosed inTable 1 and stereoisomers thereof are suitable for use in such[cyclodextrin-perfume] complexes. Such PRMs and stereoisomers thereofmay be used in combination in such [cyclodextrin-perfume] complexes.

In one aspect, the amount of total perfume based on total weight ofPolymer Assisted Delivery (PAD) Matrix Systems (including Silicones)ranges from 0.1% to about 99%, from 2.5% to about 75%, from 5% to about60%, from 5% to about 50%, from 5% to about 25%. In one aspect, theamount of total perfume based on total weight of a hot melt perfumedelivery system/perfume loaded plastic Matrix System and ranges from 1%to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% toabout 50%, from 10% to about 50%. In one aspect, the PRMs disclosed inTable 1 and stereoisomers thereof are suitable for use in such PolymerAssisted Delivery (PAD) Matrix Systems, including hot melt perfumedelivery system/perfume loaded plastic Matrix Systems. Such PRMs andstereoisomers thereof may be used in combination in such PolymerAssisted Delivery (PAD) Matrix Systems (including hot melt perfumedelivery system/perfume loaded plastic Matrix Systems).

In one aspect, the amount of total perfume based on total weight ofAmine Assisted Delivery (AAD) (including Aminosilicones) ranges from 1%to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% toabout 50%, from 5% to about 25%. In one aspect, the PRMs disclosed inTable 1 and stereoisomers thereof are suitable for use in such AmineAssisted Delivery (AAD) systems. Such PRMs and stereoisomers thereof maybe used in combination in such Amine Assisted Delivery (AAD) systems. Inone aspect, an Amine Assisted Delivery (AAD) system that may compriseone or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27,30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47,48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65,66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83,84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100,101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114,115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128,129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142,143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156,157, 158, 159, 160 and 161; stereoisomers of Table 1 PRMs 1, 2, 3, 4, 5,6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24,25, 26, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44,45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62,63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80,81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98,99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112,113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126,127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140,141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154,155, 156, 157, 158, 159, 160 and 161; and mixtures thereof is disclosed.PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 21, 22, 23, 24, 25,26, 27, 30, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46,47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66,67, 68, 69, 70, 71, 72, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89,90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 107, 108,110, 111, 112, 113, 114, 115, 117, 120, 122, 123, 125, 126, 127, 128,131, 133, 134, 137, 140, 142, 144, 145, 146, 147, 149, 150, 151, 153,154, 155, 156, 159 and 160 are ketones. PRMs 15, 16, 17, 18, 19, 20,116, 118, 119, 129, 135 and 141 are alcohols. PRMs 34, 73, 74, 75, 76,77, 91, 101, 106, 109, 121, 124, 130, 132, 136, 138, 139, 143, 148, 152,157, 158 and 161 are nitriles.

In one aspect, a Pro-Perfume (PP) Amine Reaction Product (ARP) systemthat may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 21, 22, 23, 24, 25, 26, 27, 30,31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49,50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66, 67, 68, 69,70, 71, 72, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 92, 93,94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 107, 108, 110, 111,112, 113, 114, 115, 117, 120, 122, 123, 125, 126, 127, 128, 131, 133,134, 137, 140, 142, 144, 145, 146, 147, 149, 150, 151, 153, 154, 155,156, 159 and 160 is disclosed. Such PRMs are ketones. In one aspect, theamount of total perfume based on total weight of Pro-Perfume (PP) AmineReaction Product (ARP) system ranges from 0.1% to about 99%, from about1% to about 99%, from 5% to about 90%, from 10% to about 75%, from 20%to about 75%, from 25% to about 60%.

The perfume delivery technologies also known as perfume delivery systemsthat are disclosed in the present specification may be used in anycombination in any type of consumer product, cleaning and/or treatmentcomposition, fabric and hard surface cleaning and/or treatmentcomposition, detergent, and highly compact detergent.

Perfumes

The PRMs disclosed in Table 1 may be used to formulate perfumes. Suchperfumes are combinations of PRMs that may comprise a combination ofTable 1 PRMs, or one or Table 1 PRMs and one or more additional PRMs.When used in a perfume, the Table 1 PRMs may used, based on totalperfume weight, at levels of from about 0.01% to about 50%, from about0.1% to about 15%, from about 0.1% to about 10% or even from about 0.5%to about 10%. Such perfumes may be used in multiple applicationsincluding being applied neat to a situs or used in a consumer product,cleaning and/or treatment composition, fabric and hard surface cleaningand/or treatment composition, detergent, and/or a highly compactdetergent.

Adjunct Materials

For the purposes of the present invention, the non-limiting list ofadjuncts illustrated hereinafter are suitable for use in the instantcompositions and may be desirably incorporated in certain embodiments ofthe invention, for example to assist or enhance performance, fortreatment of the substrate to be cleaned, or to modify the aesthetics ofthe composition as is the case with perfumes, colorants, dyes or thelike. It is understood that such adjuncts are in addition to thecomponents that are supplied via Applicants' perfumes and/or perfumesystems. The precise nature of these additional components, and levelsof incorporation thereof, will depend on the physical form of thecomposition and the nature of the operation for which it is to be used.Suitable adjunct materials include, but are not limited to, surfactants,builders, chelating agents, dye transfer inhibiting agents, dispersants,enzymes, and enzyme stabilizers, catalytic materials, bleach activators,polymeric dispersing agents, clay soil removal/anti-redeposition agents,brighteners, suds suppressors, dyes, additional perfume and perfumedelivery systems, structure elasticizing agents, fabric softeners,carriers, hydrotropes, processing aids and/or pigments. In addition tothe disclosure below, suitable examples of such other adjuncts andlevels of use are found in U.S. Pat. Nos. 5,576,282, 6,306,812 B1 and6,326,348 B1 that are incorporated by reference.

Each adjunct ingredient is not essential to Applicants' compositions.Thus, certain embodiments of Applicants' compositions do not contain oneor more of the following adjuncts materials: bleach activators,surfactants, builders, chelating agents, dye transfer inhibiting agents,dispersants, enzymes, and enzyme stabilizers, catalytic metal complexes,polymeric dispersing agents, clay and soil removal/anti-redepositionagents, brighteners, suds suppressors, dyes, additional perfumes andperfume delivery systems, structure elasticizing agents, fabricsofteners, carriers, hydrotropes, processing aids and/or pigments.However, when one or more adjuncts are present, such one or moreadjuncts may be present as detailed below:

Surfactants—The compositions according to the present invention cancomprise a surfactant or surfactant system wherein the surfactant can beselected from nonionic and/or anionic and/or cationic surfactants and/orampholytic and/or zwitterionic and/or semi-polar nonionic surfactants.The surfactant is typically present at a level of from about 0.1%, fromabout 1%, or even from about 5% by weight of the cleaning compositionsto about 99.9%, to about 80%, to about 35%, or even to about 30% byweight of the cleaning compositions.

Builders—The compositions of the present invention can comprise one ormore detergent builders or builder systems. When present, thecompositions will typically comprise at least about 1% builder, or fromabout 5% or 10% to about 80%, 50%, or even 30% by weight, of saidbuilder. Builders include, but are not limited to, the alkali metal,ammonium and alkanolammonium salts of polyphosphates, alkali metalsilicates, alkaline earth and alkali metal carbonates, aluminosilicatebuilders polycarboxylate compounds. ether hydroxypolycarboxylates,copolymers of maleic anhydride with ethylene or vinyl methyl ether,1,3,5-trihydroxybenzene-2,4,6-trisulphonic acid, andcarboxymethyl-oxysuccinic acid, the various alkali metal, ammonium andsubstituted ammonium salts of polyacetic acids such as ethylenediaminetetraacetic acid and nitrilotriacetic acid, as well as polycarboxylatessuch as mellitic acid, succinic acid, oxydisuccinic acid, polymaleicacid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid,and soluble salts thereof.

Chelating Agents—The compositions herein may also optionally contain oneor more copper, iron and/or manganese chelating agents. If utilized,chelating agents will generally comprise from about 0.1% by weight ofthe compositions herein to about 15%, or even from about 3.0% to about15% by weight of the compositions herein.

Dye Transfer Inhibiting Agents—The compositions of the present inventionmay also include one or more dye transfer inhibiting agents. Suitablepolymeric dye transfer inhibiting agents include, but are not limitedto, polyvinylpyrrolidone polymers, polyamine N-oxide polymers,copolymers of N-vinylpyrrolidone and N-vinylimidazole,polyvinyloxazolidones and polyvinylimidazoles or mixtures thereof. Whenpresent in the compositions herein, the dye transfer inhibiting agentsare present at levels from about 0.0001%, from about 0.01%, from about0.05% by weight of the cleaning compositions to about 10%, about 2%, oreven about 1% by weight of the cleaning compositions.

Dispersants—The compositions of the present invention can also containdispersants. Suitable water-soluble organic materials are the homo- orco-polymeric acids or their salts, in which the polycarboxylic acid maycomprise at least two carboxyl radicals separated from each other by notmore than two carbon atoms.

Enzymes—The compositions can comprise one or more detergent enzymeswhich provide cleaning performance and/or fabric care benefits. Examplesof suitable enzymes include, but are not limited to, hemicellulases,peroxidases, proteases, cellulases, xylanases, lipases, phospholipases,esterases, cutinases, pectinases, keratanases, reductases, oxidases,phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases,pentosanases, malanases, β-glucanases, arabinosidases, hyaluronidase,chondroitinase, laccase, and amylases, or mixtures thereof. A typicalcombination is a cocktail of conventional applicable enzymes likeprotease, lipase, cutinase and/or cellulase in conjunction with amylase.

Enzyme Stabilizers—Enzymes for use in compositions, for example,detergents can be stabilized by various techniques. The enzymes employedherein can be stabilized by the presence of water-soluble sources ofcalcium and/or magnesium ions in the finished compositions that providesuch ions to the enzymes.

Catalytic Metal Complexes—Applicants' compositions may include catalyticmetal complexes. One type of metal-containing bleach catalyst is acatalyst system comprising a transition metal cation of defined bleachcatalytic activity, such as copper, iron, titanium, ruthenium, tungsten,molybdenum, or manganese cations, an auxiliary metal cation havinglittle or no bleach catalytic activity, such as zinc or aluminumcations, and a sequestrate having defined stability constants for thecatalytic and auxiliary metal cations, particularlyethylenediaminetetraacetic acid,ethylenediaminetetra(methyl-enephosphonic acid) and water-soluble saltsthereof. Such catalysts are disclosed in U.S. Pat. No. 4,430,243.

If desired, the compositions herein can be catalyzed by means of amanganese compound. Such compounds and levels of use are well known inthe art and include, for example, the manganese-based catalystsdisclosed in U.S. Pat. No. 5,576,282.

Cobalt bleach catalysts useful herein are known, and are described, forexample, in U.S. Pat. Nos. 5,597,936 and 5,595,967. Such cobaltcatalysts are readily prepared by known procedures, such as taught forexample in U.S. Pat. Nos. 5,597,936, and 5,595,967.

Compositions herein may also suitably include a transition metal complexof a macropolycyclic rigid ligand—abbreviated as “MRL”. As a practicalmatter, and not by way of limitation, the compositions and cleaningprocesses herein can be adjusted to provide on the order of at least onepart per hundred million of the benefit agent MRL species in the aqueouswashing medium, and may provide from about 0.005 ppm to about 25 ppm,from about 0.05 ppm to about 10 ppm, or even from about 0.1 ppm to about5 ppm, of the MRL in the wash liquor.

Suitable transition—metals in the instant transition-metal bleachcatalyst include manganese, iron and chromium. Suitable MRL's herein area special type of ultra-rigid ligand that is cross-bridged such as5,12-diethyl-1,5,8,12-tetraazabicyclo[6.6.2]hexa-decane.

Suitable transition metal MRLs are readily prepared by known procedures,such as taught for example in WO 00/32601, and U.S. Pat. No. 6,225,464.

Method of Use

Certain of the consumer products disclosed herein can be used to cleanor treat a situs inter alia a surface or fabric. Typically at least aportion of the situs is contacted with an embodiment of Applicants'composition, in neat form or diluted in a liquor, for example, a washliquor and then the situs may be optionally washed and/or rinsed. In oneaspect, a situs is optionally washed and/or rinsed, contacted with aparticle according to the present invention or composition comprisingsaid particle and then optionally washed and/or rinsed. For purposes ofthe present invention, washing includes but is not limited to,scrubbing, and mechanical agitation. The fabric may comprise most anyfabric capable of being laundered or treated in normal consumer useconditions. Liquors that may comprise the disclosed compositions mayhave a pH of from about 3 to about 11.5. Such compositions are typicallyemployed at concentrations of from about 500 ppm to about 15,000 ppm insolution. When the wash solvent is water, the water temperaturetypically ranges from about 5° C. to about 90° C. and, when the situscomprises a fabric, the water to fabric ratio is typically from about1:1 to about 30:1.

EXAMPLES

While particular embodiments of the present invention have beenillustrated and described, it would be obvious to those skilled in theart that various other changes and modifications can be made withoutdeparting from the spirit and scope of the invention. It is thereforeintended to cover in the appended claims all such changes andmodifications that are within the scope of this invention.

Example 1 Synthesis Examples for Table 1 PRMs 1-48

Procedure for the Synthesis of Table 1 Molecule No. 31 (Exemplified fora 7.5 mmolar Scale:

In an oven dried flask were mixed under dry conditions 7.5 mmol ofbut-3-en-2-ol (1 equiv), 7.5 mmol of sodium methoxide (1 equiv), 9.0mmol of tributylamine (1.2 equiv), 7.5 mmol of 1-iodo-4-methylbenzene (1equiv) with 0.75 mmol of PdCl₂ (0.1 equiv) at room temperature in 10 mLof dry DMF. The reaction mixture was stirred while the temperature wasfirst heated to 75° C. for 3 h and for 1 h to 20° C. This temperaturecycle was repeated two more times. Then, the reaction mixture wasfiltered over a short silica path. The silica was washed with methyltert-butyl ether (MTBE; 2*3 mL). The combined organic fractions weremixed with 25 mL of 0.5 M HCl and extracted with MTBE (2*5 mL) andwashed with saturated aqueous NaHCO₃ (5 mL) and brine (5 mL). The crudeoil was obtained after drying over MgSO₄, filtration and concentration.Additional flash chromatography was performed to obtain the compound inhigh purity, with a Biotage PS1: TLC-based method calculated fromsolvent conditions 80:20-mixture petroleum ether/Ethyl Acetate.

Procedure for the Synthesis of Compound Table 1 Molecule No. 48:

Step 1, Exemplified for a 30 mmolar Scale:

In an oven dried flask were mixed under dry conditions and undernitrogen atmosphere, 30 mmol of the aldehyde (3.6 g) with 1 mL of drytetrahydrofuran (THF) at room temperature. The reaction mixture wasstirred for 10 minutes in an ice bath, before 1.1 equivalents ofiso-propylmagnesium chloride, dissolved in THF (2 M; 16.5 mL), wereadded drop wise upon this solution. The reaction was stirred for 16 h,while the temperature was allowed to come to room temperature. Then, thereaction was quenched by adding it to 17 mL of 2 M HCl, cooled with icecubes. 30 mL of methyl tert-butyl ether (MTBE) were added to thismixture and was extracted with MTBE (2*10 mL). The combined organicfractions were washed with aqueous saturated NaHCO₃ (5 mL) and brine (5mL). The crude oil was obtained after drying over MgSO₄, filtration andconcentration. The pure compound was obtained after flashchromatography, performed with a Biotage PS1: TLC-based methodcalculated from solvent conditions 9:1-mixture petroleum ether/EthylAcetate.

Step 2, Exemplified for a 24 mmolar Scale:

In an oven dried flask were mixed 24 mmol of the alcohol (5.3 g) with 30mL of dichloromethane at room temperature. The reaction mixture wasstirred for 10 minutes in an ice bath, before 1.1 equivalents ofDess-Martin periodinane (15 w % in CH₂Cl₂; 75 g), were added drop wiseupon this solution. The reaction was stirred for 4 days, while thereaction temperature was allowed to come to room temperature. Thereaction mixture was quenched by adding it to 100 mL of 1N NaOHsolution, cooled with ice cubes. The organic layer was extracted withdiethyl ether (Et₂O; 2*15 mL) and washed with aq. NaHCO₃ (10 mL) andbrine (10 mL). The crude oil was obtained after drying over MgSO₄,filtration and concentration. Then, the crude oil was dissolved again inEt₂O and kept in the freezer for 16 hours. The white precipitate wasfiltered of and the filtrate was concentrated. The pure compound wasobtained after flash chromatography, performed with a Biotage PS1:TLC-based method calculated from solvent conditions 9:1-mixturepetroleum ether/Ethyl Acetate.

Synthesis of Compounds Table 1 Molecules Numbers 2, 3 and 4:

A representative procedure is given for the synthesis of Table 1Material No. 2 by alkylation of benzyl iso-propyl ketone withbromobutane at the benzylic position:

In a flask were mixed 1.6 mmol of 3-methyl-1-phenylbutan-2-one (1equiv), 1.9 mmol of n-butylbromide (1.2 equiv), 0.022 mmol ofN-benzyltriethylammonium bromide (2 mol %) with 0.5 mL of 50% NaOH atroom temperature. The reaction mixture was vigorously stirred at roomtemperature for 1 h. The temperature of the reaction was increased to60° C., whilst stirring was continued for 5 h. Then, the reactionmixture was quenched by adding it to a cooled 1M HCl solution. 10 mL ofmethyl tert-butyl ether (MTBE) was added and the combined organicfractions were extracted with MTBE (2*5 mL) and washed with saturatedaqueous NaHCO₃ (5 mL) and brine (5 mL). The crude oil was obtained afterdrying over MgSO₄, filtration and concentration. The pure compound wasobtained after flash chromatography, performed with a Biotage PS1:TLC-based method calculated from solvent conditions 98:2-mixturepetroleum ether/Ethyl Acetate.

Modification of the representative protocol for the analogues is givenin the following Table:

Table 1 Reaction time at Molecules No. R¹Br Scale 60° C. 2¹ n-BuBr 1.6mmol  5 h 3¹ i-PrBr 1.5 mmol 24 h 4¹ EtBr   3 mmol 16 h ¹FlashChromatography was performed with a Biotage PS1: TLC-based methodcalculated from solvent conditions 98:2-mixture petroleum ether/EthylAcetate.Synthesis of Table Molecules Numbers: 15, 16, 17, 18, 19 and 20:

A representative procedure is given for the synthesis of Table 1Molecule No. 16 by addition of ethylmagnesium bromide (R²=Et; X═Br) upon3-(4-methylcyclohex-3-enyl)butanal (Limonenaldehyde; R¹═H):

A 2-necked 4-L flask was dried for 24 h at 20 mbar and 80° C. in theoven. The glassware was allowed to cool to ambient temperature undernitrogen atmosphere, before 140 gram of3-(4-methylcyclohex-3-enyl)butanal (Limonenaldehyde; 1 equiv; 0.85 mol)was dissolved in 2.8 L (5 w %) of dry 2-methyltetrahydrofuran (2-MeTHF)under dry conditions (canula). The solution was cooled to −50° C. for 1hour. Then, 280 mL of ethyl-magnesium bromide, dissolved in 2-MeTHF (3.2M; 1.06 equiv), were added via a dry dropping funnel under nitrogenatmosphere (over approximately 45 minutes; the temperature of thereaction mixture was probed and not allowed to heat over −40° C.). Thereaction was prolonged for 1 hour at −50° C. Then, the reaction wasallowed to stir overnight at 0° C. The reaction was quenched by addingit to 1 liter of 1M HCl, cooled with ice cubes (approx. 600 gram ofice). Then, the aqueous phase was extracted with 2-MeTHF (2*200 mL). Thecombined organic phases were washed with aqueous sat. bicarbonate (2*100mL) and with brine (2*100 mL). The combined fractions were dried overMgSO₄, filtered and concentrated at the rotavap. The pure compound wasobtained after distillation (111-127° C., 5-10 mbar).

Modification of the representative protocol for the analogues is givenin following Table:

Table 1 Carbonyl Reaction Molecule compound Grignard temp (° C.)Purification No. (scale) R², X time [h] protocol 15 Limonenaldehyde R² =Me 0° C., 1 h Biotage¹ (50 mmol) X = Br rt, 16 h 17 4-(4-methyl- R² = Me0° C., 1 h Biotage¹ cyclohex-3- X = Br rt, 16 h enyl)pentan-2-ol (2mmol) 16 Limonenaldehyde R² = Et −50° C., 2 h Dist (0.85 mol) X = Br 0°C., 16 h (111-127° C., 5-10 mbar) 19 Limonenaldehyde R² = i-Pr 0° C., 1h Biotage¹ (20 mmol) X = Cl rt, 16 h 18 Limonenaldehyde R² = Allyl 0°C., 1 h Biotage¹ (10 mmol) X = Cl rt, 16 h 20 Limonenaldehyde R² = t-Eu0° C., 1 h Biotage¹ (2 mmol) X = Cl rt, 16 h ¹Flash Chromatography wasperformed with a Biotage PS1: TLC-based method calculated from solventconditions 85:15-mixture petroleum ether/Ethyl Acetate.Synthesis of Table 1 Molecules Numbers 21, 22, 23, 24, 25, 26, and 27:

A representative procedure is given for the synthesis of Table 1Molecule 22 by addition of Dess-Martin periodinane upon5-(4-methylcyclohex-3-enyl)hexan-3-ol (R¹=Me):

In an oven dried flask were mixed 5.5 gram of5-(4-methylcyclohex-3-enyl)hexan-3-ol (1 equiv; 30 mmol) with 30 mL ofdichloromethane at room temperature. The reaction mixture was stirredfor 10 minutes at 0° C., before 1.1 equivalents of Dess-Martinperiodinane (15 w % in CH₂Cl₂; 94 g), were added drop wise to thissolution. The reaction was stirred for 3 days, while the reactiontemperature was allowed to come to room temperature. The reactionmixture was quenched by adding it to 100 mL of 1N NaOH solution, cooledwith ice cubes. The organic layer was extracted with diethyl ether(Et₂O; 2*15 mL) and washed with aqueous saturated NaHCO₃ (10 mL) andbrine (10 mL). The crude oil was obtained after drying over MgSO₄,filtration and concentration. Then, the crude oil was dissolved again inEt₂O and kept in the freezer for 16 hours. The white precipitate wasfiltered of and the filtrate was concentrated at the rotavap. The purecompound was obtained after flash chromatography, performed with aBiotage PS1: TLC-based method calculated from solvent conditions85:15-mixture petroleum ether/Ethyl Acetate.

Modification of the representative protocol for the analogues is givenin the following Table:

Table 1 Alcohol Reaction Molecule No. R¹ = Scale time [h] 22 Me 15 mmol0° C. rt, 72 h 23 Et 10 mmol 0° C. rt, 16 h 24 i-Pr 10 mmol 0° C. rt, 72h 26 Allyl 20 mmol 0° C. rt, 16 h 25 n-Pr  1 mmol 0° C. rt, 16 h 21 n-Am 1 mmol 0° C. rt, 16 h 27 t-Bu 20 mmol 0° C. rt, 48 h ¹FlashChromatography was performed with a Biotage PS1: TLC-based methodcalculated from solvent conditions 85:15-mixture petroleum ether/EthylAcetate.Synthesis of Table 1 Molecules Numbers 28 and 29:

A representative procedure is given for the synthesis of Table 1Molecule 29 by acetylation of 5-(4-methylcyclohex-3-enyl)hexan-3-ol:

In an oven dried flask were mixed at room temperature and under heliumatmosphere 15 mL of 2-methyltetrahydrofuran (2-MeTHF), 0.15 gram of4-(dimethylamino)pyridine (DMAP; 0.08 equiv), 8.2 gram ofN-methylmorpholine (NMM; 5.3 equiv; 8.9 mL) and 3 gram of5-(4-methylcyclohex-3-enyl)hexan-3-ol (15 mmol; 1 equiv) under dryconditions. The reaction mixture was stirred for 10 minutes in an icebath, before 7.8 gram of acetic anhydride (5 equiv; 7.17 mL) was addedvia a dropping funnel over a 10 minutes period. The reaction wasprolonged for 1 hour at 0° C. Then the ice bath was removed and thereaction was continued for 1 h at room temperature while the conversionof the reaction was followed by GC-FID, via analysis of aliquots of thereaction mixture, which were removed by syringe. Then 30 mL of water wasadded and the reaction mixture was heated to 50° C. for 15 min andextraction was performed at this temperature (2-MeTHF; 2*10 mL). Theorganic fractions were washed with sat. bi-carbonate and brine, driedover MgSO₄, filtered and concentrated at the rotavap. Additional flashchromatography was performed to obtain the compound in high purity, witha Biotage PS1: TLC-based method calculated from solvent conditions85:15-mixture petroleum ether/Ethyl Acetate.

Synthesis of Table 1 Molecules Numbers 1, 5, 6, 8, 9, 10, 11, 12, 13 and14:

A representative procedure is given for the synthesis of Table 1Molecule 10 by addition of 2-cyclopentylacetyl chloride to benzene:

A 2-L flask, dropping funnel, stiffing bar and septum were dried in theoven at 80° C. and 20 mbar for 24 h. The glassware was cooled to roomtemperature under nitrogen atmosphere, before 152 gram of aluminiumtrichloride (AlCl₃; 1.2 equiv) was dissolved in 300 mL of anhydrousbenzene. Then, 140 gram of cyclopentylacetyl chloride (1 equiv) wereadded drop wise and very slowly over a 2 h period to this reactionmixture while the temperature was controlled below 40° C. by the rate ofaddition of the acid chloride. The reaction start and progress werefollowed by the gas evolvement. Then, the reaction mixture was continuedat 45° C. for 16 h. The reaction mixture was quenched by adding it to alarge quantity of crushed ice (1.5 kg). 1 Liter of demineralised waterwas added, while controlling the temperature with ice. A whitesuspension was formed. The glassware was washed with 100 mL of methyltert-butyl ether (MTBE) and the combined organic layers were filteredand extracted with MTBE (2*100 mL). Then the organic layers were washedwith aqueous NaHCO₃ solution and brine. The organic fractions werecollected, dried over Na₂SO₄, filtered and dried in vacuo (70° C. at 15mbar) to afford a red oil. This oil was mixed with 10 w % of activecarbon and stirred at room temperature for 16 h. Then the mixture wasfiltered over a short Celite path and the glassware and filter wererinsed with 100 mL of ligroin. The organic fractions were combined anddried at the rotavap, affording a yellow oil.

Modification of the representative protocol for the analogues is givenin the following Table:

Table 1 Reaction Purifica- Molecule Acid Chloride temp (° C.) tion No.(scale) Aryl ring time [h] protocol 1 Cyclohexylacetyl benzene rt, 24 h— chloride (30 mmol) 5 Cyclohexylacetyl toluene rt, 4 h — chloride (10mmol) 6 Cycloheptylacetyl benzene rt, 24 h — chloride (5 mol) 10Cyclopentylacetyl benzene rt — chloride 45° C., 16 h (500 mmol) 113-cyclohexyl- benzene rt Recryst propanoyl chloride 45° C., 16 h (Et₂O)(50 mmol) 12 3-cyclohexyl- ethylbenzene rt, 72 h Biotage¹ propanoylchloride (50 mmol) 13 3-cyclohexyl- toluene rt, 72 h Recryst propanoylchloride (Et₂O) (50 mmol) 14 3-cyclohexyl- mesitylene rt, 72 h Biotage¹propanoyl chloride (30 mmol) 8 Cyclopentylacetyl ethylbenzene 0° C.Biotage¹ chloride rt, 16 h (15 mmol) 9 Cyclopentylacetyl mesitylene 0°C. Biotage¹ chloride rt, 16 h (15 mmol) ¹Flash Chromatography wasperformed with a Biotage PS1: TLC-based method calculated from solventconditions 95:5-mixture petroleum ether/Ethyl Acetate.Synthesis of Table 1 Molecules Numbers 30, 33, 34, 37, 38, 39, 40 and44:

A representative procedure is given for the synthesis of Table 1Molecule 33 with para-Tolualdehyde (R¹, R², R⁴═H; R³=Me) and methylethyl ketone (R⁵=Me):

In a reaction flask were mixed at room temperature 10.61 mol of ketone(1.7 equiv), 6.24 mol of aldehyde (1 equiv) and 0.5 mol % of RuCl₃.nH₂O(9.2 gram). Then, the reaction mixture was stirred whilst thetemperature of the oil bath was increased to 115-130° C. Aliquots of thereaction mixture were removed by syringe and analyzed by GC-FID. Basedon the GC-results, the reaction was allowed to progress (in thisspecific case) until 85% of the starting material was converted over aperiod of 7 days. Then, the reaction mixture was cooled to roomtemperature before 1.5 L of toluene was added. The organic phase wasextracted with aqueous saturated bicarbonate (4*750 mL). Each time, theaqueous phase was washed with toluene (2*100 mL). After this washing,all the organic phases were combined and washed once more with aqueoussaturated bicarbonate (750 mL) and with brine (3*250 mL).

Then, a series of bisulfite washings were performed on the crude oilobtained after concentration of the organic phase at the rotavap (70° C.at 100 mbar). The crude oil was dissolved in equal amounts of tolueneand mixed at room temperature with a 40 w % of aqueous NaHSO₃ (1.5 equivof sodium bisulfite as calculated for the amount of aldehyde present inthe crude oil). This mixture was vigorously stirred for 1 hour at roomtemperature before the organic fraction was decanted. The aqueous layerwas extracted once with 50 mL of toluene.

The combined organic fractions were washed with aqueous saturatedbicarbonate (2*25 mL) and brine (2*25 mL), dried over MgSO₄, filteredand concentrated. The bisulfite washings were repeated until the totalamount of aldehyde was below 4% (in this specific case, three washingswere performed). The compound was purified via distillation (4-7 mbar;oil bath 115-160° C.) and recrystallisation from methyl tert-butyl ether(MTBE; 2*200 w %).

Modification of the representative protocol for the analogues is givenin the following Table:

Table 1 Mole- Ketone Reaction cule Aldehyde R⁵ temp (° C.) PurificationNo. R¹,R²,R³,R⁴ (equiv) time [d] protocol 30 R¹,R²,R³,R⁴ = H R⁵ = Me(120) [1] Biotage¹ (0.5 equiv) 33 R¹,R²,R⁴ = H R⁵ = Me (120) [7]Distillation, R³ = Me (1.7 equiv) recrystal- lisation 34 R¹,R²,R⁴ = H R⁵= Me (120) [7] Biotage¹ R³ = CN (1 equiv) 37 R²,R³,R⁴ = H R⁵ = Me (120)[14] Biotage¹, R¹ = Me (2 equiv)² Dist (102-121° C.; 3-13 mbar) 38R¹,R³,R⁴ = H R⁵ = Me (125) [1] Biotage¹ R² = Me (0.5 equiv) 39 R¹,R²,R⁴= H R⁵ = Me (125) [1] Biotage¹ R³ = OMe (0.5 equiv) 40 R¹,R²,R⁴ = H R⁵ =Et (130) [4] Biotage¹, R³ = Me (0.5 equiv) Dist (110-135° C.; 3-5 mbar)44 R¹,R³,R⁴ = Me R⁵ = Me (125) [7] Dist R² = H (2 equiv)² (91-93° C.;0.1-0.4 mbar) ¹Flash Chromatography was performed with a Biotage PS1:TLC-based method calculated from solvent conditions 9:1-mixturepetroleum ether/Ethyl Acetate. ²more RuCl₃ catalyst was added.Synthesis of Table 1 Molecules Numbers 32, 35, 36, 41, 42, 43, 45, 46and 47:

A representative procedure is given for the synthesis of Table 1Molecule 35 by condensation of benzaldehyde (R¹, R², R³, R⁴═H) with2-pentanone (R⁵=Et; R⁶, R⁷═H):¹ ¹ In analogy to: Cao, Y.-Q.; Dai, Z.;Zhang, R. and Chen, B.-H. Synth. Commun., 2005, 35, 1045-1049.

In a 2-L flask, 330 gram of benzaldehyde (1 equiv) was mixed with 1Liter of 2-pentanone (3 equiv). The reaction mixture was cooled to 5-10°C. and thoroughly stirred, before 40 mL of NaOH, 50 w % solution inwater (0.5 equiv, 61 g), was slowly added in one portion. After 30minutes, the temperature of the reaction mixture was allowed to rise to20° C. The reaction was continued for 5 hours at ambient temperature.Then, the reaction was quenched by adding the reaction mixture to a 2 MHCl solution which was cooled with equal amounts of ice. Afterextraction with 2-pentanone (2*100 mL), the combined organic fractionswere washed with saturated, aqueous bicarbonate solution (50 mL) andbrine (50 mL). The organic fractions were combined and concentrated atthe rotavap, resulting in a yellow oil. This crude oil was poured in anErlenmeyer, containing 400 mL of diethyl ether (Et₂O). The flask wasrinsed with 100 mL of Et₂O, which was added to the organic phase. Then,500 mL of aqueous saturated NaHSO₃ solution was added to the combinedorganic fractions at room temperature. This mixture was vigorouslystirred for 1 hour before the organic phase was decanted and washed withsaturated, aqueous bicarbonate solution (25 mL) and brine (25 mL). Theyellow oil obtained was concentrated at the rotavap and dried at themembrane pump (70° C. at 4 mbar). The compound was first purified viadistillation (115-125° C., 1-3 mbar). Afterwards, two additionalbisulfite washings were performed.

Modification of the representative protocol for the analogues is givenin the following Table:

Com- pound Aldehyde Ketone Purification Number R¹,R²,R³,R⁴ R⁵ equivketone protocol 32 R¹,R³,R⁴ = H R⁵ = Me 2.8 equiv Biotage¹ R² = Me R⁶,R⁷= H 36 R²,R³,R⁴ = H R⁵ = Me 2.8 equiv Biotage¹ R¹ = Me R⁶,R⁷ = H 35R¹,R²,R³,R⁴ = H R⁵ = Et 3 equiv Dist R⁶,R⁷ = H (115-125° C.; 1-3 mbar)47 R¹,R³,R⁴ = H R⁵ = Et 3.5 equiv Biotage¹ R² = Me R⁶,R⁷ = H 43 R¹,R³,R⁴= Me R⁵ = Et 3 equiv Dist R² = H R⁶,R⁷ = H (105-125° C.; 0.1-0.4 mbar)recryst (MTBE) 41 R²,R³,R⁴ = H R⁵ = Et 3.5 equiv Dist R¹ = Me R⁶,R⁷ = H(90-95° C.; 0.01-0.04 mbar) 42 R¹,R³,R⁴ = Me R⁵ = Et 3 equiv Dist R² = HR⁶,R⁷ = H (91-93° C.; 0.1-0.4 mbar) 45 R²,R³ = H R⁵ = Et 3 equiv DistR¹,R⁴ = Me R⁶,R⁷ = H (105-125° C.; 0.05-0.2 mbar) 46 R²,R³ = H R⁵ = Me 6equiv Dist R¹,R⁴ = Me R⁶,R⁷ = H (80-90° C.; 0.02-0.1 mbar) ¹FlashChromatography was performed with a Biotage PS1: TLC-based methodcalculated from solvent conditions 7:3-mixture petroleum ether/EthylAcetate.Synthesis of Table 1 Molecule Number 7:

Reaction Components

1 Cyclopentylacetyl C₇H₁₁OCl 1 equiv.-10 g Chloride 146.61 g/mol 2Toluene C₇H₉ 30 mL 92.11 g/mol 3 Aluminium AlCl₃ 1.2 equiv.-10.9 gChloride 133.34 g/mol

Glassware for parallel synthesis (flask, condenser and dropping funnel),stirring bar, septum and syringe were dried in the oven at 80° C. and 20mbar for 24 h. All the glassware was mounted as foreseen and was cooleddown to room temperature under Argon atmosphere, before AlCl₃ wasdissolved in the toluene. The reaction vessel was placed in an ice bathand the acid chloride was added drop wise after some time. Even thoughthe acid chloride was added very slow via the dropping funnel a slightlyexothermic reaction started and a lot of gas evolved. Every 2 minutesthe pressure was released. The reaction mixture was stirred at roomtemperature overnight, before the reaction was checked via GC MS. Thenthe reaction mixture was quenched in demineralised water with 5 icecubes in it. A white suspension was formed (exothermic; additional icecubes were added). The glassware was washed with 25 mL of Et₂O and thecombined organic layers were filtered and extracted with ether (2*20mL). Then the organic layers were treated with 2*25 mL of aqueous NaHCO₃solution and this aqueous layer was extracted again with diethyl ether(2*10 mL). Then, the organic fractions were collected, dried overNa₂SO₄, filtered and dried in vacuum (low pressure; high temperatureresulting in a dark oil formed. The compound was placed in the fridgeand solidified after some time. It was tried to purify the ketone viare-crystallisation. First it was dissolved in the minimal amount ofEt₂O. Upon cooling it solidified after a few hours. This procedure wasrepeated two times resulting in colourless crystals.

Synthesis of Table 1 Molecule Number 49, 50 & 61:

Step 1.

Step 2.

applied Compound scale (mmol Number R substrate) 49 t-Bu 10 50 i-Pr 1161 Me 10

A representative procedure is given for the synthesis of Table 1Molecule 50.

Step 1.

A solution of n-butyllithium (2.2M in cyclohexane—1 eq.) was added dropwise to an ice cold solution of diisopropylamine (1 eq.) in dry THF.After stirring for 10 minutes at this temperature, propionitrile (5 eq.)was added to the mixture. Prenyl bromide (1 eq.) was added after anothermixing of 10 minutes at 0° C. Reaction conversion was followed by GC-MSand seen as complete after 15 minutes stirring at 0° C.

The reaction was quenched by addition of saturated NH₄Cl aqueoussolution and extracted with Et₂O. The combined organic layers were driedover MgSO₄ and concentrated under reduced pressure. The resulting oilwas purified using a quick filtration over silica by elution with apetroleum ether—Et₂O mixture (9-1). Concentration of the eluent underreduced pressure resulted in the compound as a colorless oil.

Step 2.

A methyllithium solution (1.2 equiv.) was added drop wise to a solutionof the nitrile (1 eq.) in dry THF (0.5M) at −20° C. After stiffing for15 minutes at −10/−20° C., full conversion was observed by GC-MS. Thereaction was quenched with a H₂SO₄ solution (2M—2 eq.) and stirred atambient temperature till full hydrolysis of the in situ formed imine wasobserved. The mixture was then extracted with Et₂O and washed with asaturated NaHCO₃ aqueous solution. The combined organic phases weredried over MgSO₄ and concentrated under reduced pressure. The resultingoil was purified with column chromatography by eluting with a petroleumether—MTBE mixture (95-5). Concentration of the desired fractions underreduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 52:

Compound 52 was synthesized starting from 20 mmol4,4-dimethyl-3-oxopentanoate.

Step 1.

To a solution of 4,4-dimethyl-3-oxopentanoate (1 eq.) and K₂CO₃ (2.2eq.) in dry acetone (0.9 M) was added iodomethane (3.3 eq.) at 60° C.The mixture was stirred for 16 hours at the same temperature and driedover MgSO₄ after cooling to ambient temperature. The organic mixture wasconcentrated under reduced pressure to yield the product without furtherpurification.

Step 2.

The β-keto-ester (1 eq.) formed in step 1 was solved in MTBE (0.6 M) andsodium t-butoxide (1.1 eq.) and prenyl bromide (1.5 eq.) were added atroom temperature. The resulting mixture was stirred for 16 hours at thesame temperature and quenched with an aqueous H₂SO₄ solution (0.5 M).After extracting the mixture with MTBE, the collected organic layerswere dried over MgSO₄ and concentrated under reduced pressure. Theresulting oil was purified by column chromatography using a petroleumether—MTBE mixture (95-5) as eluens. Concentration of the eluent underreduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 53:

Compound 53 was synthesized starting from 45 mmol3,3-dimethyl-2-butanone.

A solution of n-butyllithium (2.2M in cyclohexane—2 eq.) was added dropwise to an ice cold solution of diisopropylamine (2 eq.) in dry THF (0.5M). After stiffing for 10 minutes at this temperature,3,3-dimethyl-2-butanone (1 eq.) was added to the mixture. Prenyl bromide(2 eq.) was added after another mixing of 10 minutes at 0° C. Reactionconversion was followed by GC-MS and seen as complete after 12 h atambient temperature.

The reaction was quenched by addition of saturated NH₄Cl aqueoussolution and extracted with Et₂O. The combined organic layers were driedover MgSO₄ and concentrated under reduced pressure. The resulting oilwas purified by column chromatography using a petroleum ether-MTBEmixture (95-5) as eluens. Concentration of the eluent under reducedpressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 63:

Compound 63 was synthesized starting from 15 mmol lavandulol.

To a stirred solution of lavandulol (1 eq.) in dry CH₂Cl₂ (0.2 M) atambient temperature was added NaHCO₃ (4 eq.) and Dess-Martin periodane(1.5 eq.). Complete reaction conversion was observed via GC-MS after 1hour stiffing at the same temperature. The reaction was quenched by theaddition of petroleum ether and filtered over a silica gel plug andrinsed with a petroleum ether—Et₂O mixture (9-1). The crude aldehyde isobtained by concentration under reduced pressure.

This aldehyde was resolved in t-BuOH (0.2 M) and 2-methyl-2-butene (0.6M). The resulting solution was cooled to 0° C. and a solution of NaClO₂(10 eq.) and NaH₂PO₄ (8 eq.) in water (0.3 M) was added. The reactionmixture was allowed to warm to ambient temperature and stirred for 2hours. The resulting mixture was quenched by the addition of a phosphatebuffer (pH 7). The two layers were separated and the aqueous layer wasextracted with CH₂Cl₂. The combined organic phases were dried over MgSO₄and concentrated under reduced pressure. Column chromatography using theeluent petroleum ether—Et₂O (1-1) resulted in the compound as acolorless oil.

Synthesis of Table 1 Molecule Number 73, 74, 75, 76, 77, 91, 106, 109,121, 124, 130, 132, 136, 138, 139, 143, 148, 152, 157, 158 & 161:

applied scale Compound (mmol Number R¹ R² substrate) 73 R¹ = Me, H

28

74 2R¹ = cyclopentyl

54 75 2R¹ = cyclohexyl

64 76 2R¹ = cyclopropyl

63 77 2R¹ = cyclobutyl

600 91 Me

165 106 Me

137 109 2R¹ = cyclopropyl

68 121 Me

72 124 Me

55 130 Me

28 132 2R¹ = cyclobutyl

49 136 2R¹ = cyclopropyl

54 138 Me

55 139 Me

55 143 Me

55 148 Me

25 152 Me

55 157 Me

55 158 Me

55 161 Me

26 (used for synthesis compounds 98 + 99) Me

26 (used for synthesis compounds 115) Me

55

A representative procedure is given for the synthesis of Table 1Molecule 152.

A solution of n-butyllithium (2.2M in cyclohexane—1 eq.) was added dropwise to an ice cold solution of diisopropylamine (1 eq.) in dry THF (0.5M). After stirring for 10 minutes at this temperature, i-butyronitrile(1 eq.) was added to the mixture. 3-Bromocyclohex-1-ene (1 eq.) wasadded after another mixing of 10 minutes at 0° C. Reaction conversionwas followed by GC-MS and seen as complete after 15 minutes stirring at0° C.

The reaction was quenched by addition of a saturated NH₄Cl aqueoussolution and extracted with Et₂O. The combined organic layers were driedover MgSO₄ and concentrated under reduced pressure. The resulting oilwas purified using a quick filtration over silica by elution with apetroleum ether—Et₂O mixture (9-1). Concentration of the eluent underreduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 51, 54, 55, 56, 57, 58, 59, 60, 62,64, 65, 66, 67, 68, 69, 70, 71, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87,88, 89, 90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 107,108, 110, 111, 112, 113, 114, 115, 117, 122, 126, 127, 128, 131, 133,134, 137, 142, 149, 150, 151, 153, 154, 155, 156, 159 & 160:

Compound applied scale Number Nitrile R³ (mmol substrate) 51 91 t-Bu 654 75 Me 5 55 75 Et 6 14 56 75 i-Pr Compound 62 was isolated as sideproduct in the imine hydrolysis to compound 56. 57 91 Et 16 58 74 Me 1259 74 Et 12 60 73 Me 8 64 74 i-Pr 15 65 73 Et 10 66 73 i-Pr 10 67 91s-Bu 15 68 76 Me 7 69 76 s-Bu 15 70 76 i-Pr 15 71 76 n-Bu 15 78 77 s-Bu11 79 77 Me 13 80 [935-44-4] s-Bu 10 81 77 n-Bu 11 82 77 i-Pr 13 83[935-44-4] Et 14 84 [935-44-4] i-Pr 13 85 76 Et 14 86 76 i-Bu 13 87[71172-78-6] Et 11 88 [71172-78-6] s-Bu 10 89 [15760-35-7] Me 10 90[14377-68-5] n-Bu 10 92 91 n-Bu 11 93 91 i-Bu 11 94 74 n-Bu 10 95 74i-Bu 10 96 76 t-Bu 12 97 [71172-78-6] i-Pr 11 98 described in Me 9nitrile synthesis 99 protocol s-Bu 8 100 101 i-Pr 11 102 101 Me 12 103101 Et 13 104 [68983-70-0] Me 11 107 106 Me 12 108 106 Et 12 110 106s-Bu 129 111 109 Et 11 112 109 Me 11 113 109 s-Bu 10 114 109 i-Pr 11 115[35863-45-7] i-Bu 10 117 77 Et 167 122 121 Et 10 126 124 s-Bu 9 127 121Me 10 128 124 Et 10 131 130 i-Pr 10 133 132 Me 11 134 132 i-Pr 19 137136 Me 12 142 139 Me 9 149 148 Et 9 150 148 n-Bu 9 151 143 Me 12 153 152i-Bu 11 154 143 n-Bu 9 155 152 Et 12 156 143 Et 10 159 158 n-Bu 11 160157 Me 11

A representative procedure is given for the synthesis of Table 1Molecule 151.

A methyllithium solution (1.2 equiv.) was added drop wise to a solutionof the nitrile (1 eq.) in dry THF (0.5M) at −20° C. After stiffing for15 minutes at −10/−20° C., full conversion was observed by GC-MS.

The reaction was quenched with a H₂SO₄ solution (2M—2 eq.) and stirredat ambient temperature till full hydrolysis of the in situ formed iminewas observed. The mixture was then extracted with Et₂O and washed with asaturated NaHCO₃ aqueous solution. The combined organic phases weredried over MgSO₄ and concentrated under reduced pressure. The resultingoil was purified using a quick filtration over silica gel by elutingwith a petroleum ether—Et₂O mixture (9-1). Concentration of the eluentunder reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 72, 105, 120, 123, 144, 145, 146 &147:

Step 1.

Step 2.

Step 3.

Compound applied scale Number RM (mmol substrate) 72 EtMgBr 146 105 PhLi7 120 VinylMgBr 100 123 cyclopentylMgCl 5 144 n-BuLi 6 145 i-PrMgCl 6146 i-BuLi 6 147 t-BuLi 5

A representative procedure is given for the synthesis of Table 1Molecule 72.

Step 1.

To a solution of the phosphonium bromide [50889-29-7] (1.2 eq.) in dryTHF (0.3 M) was added KHMDS (Potassiumhexamethyldisilazane—2.4 eq.) atambient temperature. After stirring for 30 minutes at the sametemperature, a solution of acetone (1 eq.) in dry THF (0.3 M) was addeddrop wise. The mixture was stirred for 3 hours, quenched with water (0.3M) and extracted with Et₂O. The resulting water layer was acidified witha HCl aqueous solution (10%) till pH 2 was obtained. This mixture wasextracted with Et₂O and the extracts were dried over MgSO₄ andconcentrated under reduced pressure. The resulting oil was purifiedusing a quick filtration over silica gel by eluting with a petroleumether—Et₂O mixture (1-1). Concentration under reduced pressure resultedin the compound as a slightly yellow oil.

Step 2.

To a solution of the acid formed in step 1 (1 eq.) in dry CH₂Cl₂ (0.5 M)was added 1,1′-carbonyldiimidazole (1 eq.) at ambient temperature. Themixture was stirred for 15 minutes and N,O-Dimethylhydroxylaminehydrochloride (1 eq.) was added. Stirring was continued at the sametemperature for 1 hour and the mixture was quenched with an aqueous HClsolution (1M—1.1 eq.). The aqueous layer was extracted with Et₂O, washedwith NaHCO₃ and dried over MgSO₄. Concentration under reduced pressureresulted in the compound as a colorless oil.

Step 3.

The Weinreb amide formed in step 2 was solved in dry THF (0.5 M) andcooled to −15° C. A solution of EtMgBr (1M—1.5 eq.) was added drop wiseto the mixture. Complete reaction conversion was observed with GC-MSafter 10 minutes stirring at −10/−15° C. This reaction mixture wasquenched with a saturated aqueous NH₄Cl solution, extracted with Et₂O;dried over MgSO₄ and concentrated under reduced pressure. The resultingoil was purified using a quick filtration over silica gel by elutingwith a petroleum ether—Et₂O mixture (9-1). Concentration under reducedpressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 101:

Compound 101 was synthesized starting from 100 mmol nitrile [2947-60-6].

To a solution of diisopropylamine (2.2 eq.—28.1 mL) in dry THF (0.5 M)was added drop wise a solution of n-butyllithium (2.2 eq.—100 mL 2.2 M)at 0° C. 2-m-Tolylacetonitrile (1 eq.—13 mL) was added to the solutionafter 10 minutes of stirring at the same temperature. A supplementarystirring for 10 minutes was followed by the drop wise addition ofiodomethane (2.5 eq.—15.6 mL). Reaction completion was observed after 10minutes stirring at 0° C. The mixture was quenched with an aqueoussolution of NH₄Cl, extracted with Et₂O, dried over MgSO₄ andconcentrated under reduced pressure. The resulting oil was purifiedusing a quick filtration over silica gel by eluting with a petroleumether—Et₂O mixture (9-1). Concentration under reduced pressure resultedin the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 116, 118 & 129:

Compound applied scale Number R¹ R² R³ R⁴ (mmol substrate) 116 2R¹ =cyclopropyl prenyl Me Me 13 118 2R¹ = cyclobutyl prenyl Et Me 8 129 2R¹= cyclobutyl prenyl Et n-Bu 10

A representative procedure is given for the synthesis of Table 1Molecule 116.

To a solution of compound 68 (1 eq.) in dry THF (0.5 M) was added asolution of methylmagnesium bromide (1.5 eq.—3M) at −20° C. The reactionmixture was allowed to warm to ambient temperature and stiffing wascontinued for 2 hours. The reaction was quenched with the addition of asaturated aqueous NH₄Cl solution and extracted with Et₂O. The combinedorganic layers were dried over MgSO₄ and concentrated under reducedpressure. The resulting oil was purified by column chromatography usingthe eluens petroleum ether—MTBE (95-5). Concentration of the requiredfractions resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 119, 135 & 141:

applied scale Compound (mmol Number Ketone R¹ R² R³ substrate) 119 1172R¹ = prenyl Et 8 cyclobutyl 135 134 2R¹ = cyclobutyl

i-Pr 7 141 140 2R¹ = cyclopropyl

allyl 11

A representative procedure is given for the synthesis of Table 1Molecule 119.

To a solution of compound 117 (1 eq.) in dry Et₂O (0.5 M) was addedportion wise lithium-aluminiumhydride (1 eq.) at 0° C. Reactioncompletion was observed by GC-MS after 15 minutes of stirring at ambienttemperature. The mixture was cooled to 0° C. and consequently was added:water (same amount of mL as mg hydride used), 15% NaOH solution (sameamount of mL as mg hydride used) & water (2 times amount of mL as mghydride used). This quenching was followed by stirring for 1 hour atambient temperature. The resulting mixture was filtered over celite andthe filter was washed with Et₂O. Concentration of the filtrate underreduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 125:

Compound 125 was synthesized starting from 11 mmol iso-butyronitrile.

Step 1.

4-Fluoro-2-methylanisole (1 eq.) was solved in dry THF (0.7 M) and KHMDS(Potassiumhexa-methyldisilazane—1.5 eq.) was added at room temperature.The mixture was heated to 60° C. after the addition of iso-butyronitrile(4 eq.). Refluxing was continued for 12 hours. The reaction was quenchedwith an aqueous HCl solution (1M) and extracted with Et₂O. The organiclayers were dried over MgSO₄ and concentrated under reduced pressure (1mbar at 55° C.). The resulting oil was purified using a quick filtrationover silica gel by eluting with a petroleum ether—Et₂O mixture (9-1).Concentration under reduced pressure resulted in the compound as acolorless oil.

Step 2.

The nitrile formed in step 1 was solved in dry THF (0.5 M) and cooled to−20° C. A solution of methyllithium (1.3 eq.—1.6 M) was added drop wise.Reaction completion was observed after 10 minutes stiffing at −20° C.The reaction was quenched with a H₂SO₄ solution (2M—2 eq.) and stirredat ambient temperature till full hydrolysis of the in situ formed iminewas observed (over night ambient temperature). The mixture was thenextracted with Et₂O and washed with a saturated NaHCO₃ aqueous solution.The combined organic phases were dried over MgSO₄ and concentrated underreduced pressure. The resulting oil was purified using a quickfiltration over silica gel by eluting with a petroleum ether—Et₂Omixture (9-1). Concentration of the eluent under reduced pressureresulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 140:

Compound 140 was synthesized starting from 24 mmol acid [6120-95-2].

Step 1.

To a solution of 1-Phenyl-1-cyclopropanecarboxylic acid (1 eq.) in dryCH₂Cl₂ (0.5 M) was added 1,1′-carbonyldiimidazole (1 eq.) at ambienttemperature. The mixture was stirred for 15 minutes andN,O-dimethylhydroxylamine hydrochloride (1 eq.) was added. Stirring wascontinued at the same temperature for 1 hour and the mixture wasquenched with an aqueous HCl solution (1M—1.1 eq.). The aqueous layerwas extracted with Et₂O, washed with NaHCO₃ and dried over MgSO₄.Concentration under reduced pressure resulted in the compound as acolorless oil.

Step 2.

The Weinreb amide formed in step 2 was solved in dry THF (0.5 M) andcooled to −15° C. A solution of EtMgBr (1M—1.5 eq.) was added drop wiseto the mixture. Complete reaction conversion was observed with GC-MSafter 10 minutes stirring at −10/−15° C. This reaction mixture wasquenched with a saturated aqueous NH₄Cl solution, extracted with Et₂O;dried over MgSO₄ and concentrated under reduced pressure. The resultingoil was purified using a quick filtration over silica gel by elutingwith a petroleum ether—Et₂O mixture (9-1). Concentration under reducedpressure resulted in the compound as a colorless oil.

Example 2 Preformed Amine Reaction Product

The following ingredients are weighted off in a glass vial:

50% of the perfume material comprising one or more Table 1 PRMs

50% of Lupasol WF (CAS #09002-98-6) from BASF, is put at 60° C. in warmwater bath for 1 hour before use. Mixing of the two ingredients was doneby using the Ultra-Turrax T25 Basic equipment (from IKA) during 5minutes. When the mixing is finished the sample is put in a warm waterbath at 60° C. for ±12 hours. A homogenous, viscous material isobtained.

In the same way as described above different ratios between thecomponents can be used:

Weight % Perfume Material 40 50 60 70 80 Lupasol WF 60 50 40 30 20

Example 3 84 wt % Core/16 wt % Wall Melamine Formaldehyde (MF) Capsule(PAD Reservoir System

25 grams of butyl acrylate-acrylic acid copolymer emulsifier (ColloidC351, 25% solids, pka 4.5-4.7, (Kemira Chemicals, Inc. Kennesaw, Ga.U.S.A.) is dissolved and mixed in 200 grams deionized water. The pH ofthe solution is adjusted to pH of 4.0 with sodium hydroxide solution. 8grams of partially methylated methylol melamine resin (Cymel 385, 80%solids, (Cytec Industries West Paterson, N.J., U.S.A.)) is added to theemulsifier solution. 200 grams of perfume oil comprising one or moreTable 1 PRMs is added to the previous mixture under mechanical agitationand the temperature is raised to 50° C. After mixing at higher speeduntil a stable emulsion is obtained, the second solution and 4 grams ofsodium sulfate salt are added to the emulsion. This second solutioncontains 10 grams of butyl acrylate-acrylic acid copolymer emulsifier(Colloid C351, 25% solids, pka 4.5-4.7, Kemira), 120 grams of distilledwater, sodium hydroxide solution to adjust pH to 4.8, 25 grams ofpartially methylated methylol melamine resin (Cymel 385, 80% solids,Cytec). This mixture is heated to 70° C. and maintained overnight withcontinuous stirring to complete the encapsulation process. 23 grams ofacetoacetamide (Sigma-Aldrich, Saint Louis, Mo., U.S.A.) is added to thesuspension. An average capsule size of 30 μm is obtained as analyzed bya Model 780 Accusizer.

Example 4 Process of Making a Polymer Assisted Delivery (PAD) MatrixSystem

A mixture comprising 50% of a perfume composition comprising one or moreTable 1 PRMs, 40% of carboxyl-terminated Hycar®1300×18 (CAS#0068891-50-9) from Noveon, (put at 60° C. in warm water bath for 1 hourbefore mixing) and 10% of Lupasol® WF (CAS #09002-98-6) from BASF (putat 60° C. in warm water bath for 1 hour before mixing). Mixing isachieved by mixing for five minutes using a Ultra-Turrax T25 Basicequipment (from IKA). After mixing, the mixture is put in a warm waterbath at 60° C. for ±12 hours. A homogenous, viscous and sticky materialis obtained.

In the same way as described above different ratios between thecomponents can be used:

Weight % Perfume composition 40 50 60 70 80 Lupasol ® WF 12 10 8 6 4Hycar ® 48 40 32 24 16 CTBN1300X18

Weight % Perfume composition 50 50 50 50 50 50 50 50 Lupasol ® WF 2.5 57.5 10 12.5 15 17.5 20 Hycar ® 47.5 45 42.5 40 37.5 35 32.5 30 CTBN1300X18

Example 5 Product Formulation

Non-limiting examples of product formulations containing PRMs disclosedin the present specification perfume and amines summarized in thefollowing table.

EXAMPLES (% wt) XI XII XIII XIV XV XVI XVII XVIII XIX XX FSA ^(a) 1416.47 14 12 12 16.47 — — 5 5 FSA ^(b) — 3.00 — — — FSA ^(c) — — 6.5 — —Ethanol 2.18 2.57 2.18 1.95 1.95 2.57 — — 0.81 0.81 Isopropyl — — — — —— 0.33  1.22 — — Alcohol Starch ^(d) 1.25 1.47 2.00 1.25 — 2.30 0.5 0.70 0.71 0.42 Amine * 0.6 0.75 0.6 0.75 0.37 0.60 0.37 0.6 0.37 0.37Perfume X ^(e) 0.40 0.13 0.065 0.25 0.03 0.030 0.030  0.065 0.03 0.03Phase 0.21 0.25 0.21 0.21 0.14 — —  0.14 — — Stabilizing Polymer ^(f)Suds — — — — — — — 0.1 — — Suppressor ^(g) Calcium 0.15 0.176 0.15 0.150.30 0.176 — 0.1-0.15 — — Chloride DTPA ^(h) 0.017 0.017 0.017 0.0170.007 0.007 0.20 — 0.002 0.002 Preservative 5 5 5 5 5 5 — 250 ^(j)   5 5(ppm) ^(i, j) Antifoam ^(k) 0.015 0.018 0.015 0.015 0.015 0.015 — —0.015 0.015 Dye (ppm) 40 40 40 40 40 40 11 30-300 30 30 Ammonium 0.1000.118 0.100 0.100 0.115 0.115 — — — — Chloride HCl 0.012 0.014 0.0120.012 0.028 0.028 0.016  0.025 0.011 0.011 Structurant ^(l) 0.01 0.010.01 0.01 0.01 0.01 0.01  0.01 0.01 0.01 Additional 0.8 0.7 0.9 0.5 1.20.5 1.1 0.6 1.0 0.9 Neat Perfume Deionized † † † † † † † † † † Water^(a) N,N-di(tallowoyloxyethyl)-N,N-dimethylammonium chloride. ^(b)Methyl bis(tallow amidoethyl)2-hydroxyethyl ammonium methyl sulfate.^(c) Reaction product of Fatty acid with Methyldiethanolamine in a molarratio 1.5:1, quaternized with Methylchloride, resulting in a 1:1 molarmixture of N,N-bis(stearoyl-oxy-ethyl) N,N-dimethyl ammonium chlorideand N-(stearoyl-oxy-ethyl) N,-hydroxyethyl N,N dimethyl ammoniumchloride. ^(d) Cationic high amylose maize starch available fromNational Starch under the trade name CATO ®. ^(e) Perfume comprising oneor more Table 1 PRMs. ^(f) Copolymer of ethylene oxide and terephthalatehaving the formula described in U.S. Pat. No. 5,574,179 at col. 15,lines 1-5, wherein each X is methyl, each n is 40, u is 4, each R1 isessentially 1,4-phenylene moieties, each R2 is essentially ethylene,1,2-propylene moieties, or mixtures thereof. ^(g) SE39 from Wacker ^(h)Diethylenetriaminepentaacetic acid. ^(i) KATHON ® CG available from Rohmand Haas Co. “PPM” is “parts per million.” ^(j) Gluteraldehyde ^(k)Silicone antifoam agent available from Dow Corning Corp. under the tradename DC2310. ^(l) Hydrophobically-modified ethoxylated urethaneavailable from Rohm and Haas under the tradename Aculan 44. * One ormore materials comprising an amine moiety as disclosed in the presentspecification. † balance

Example 6 Dry Laundry Formulations

% w/w granular laundry detergent composition Component A B C D E F GBrightener 0.1 0.1 0.1 0.2 0.1 0.2 0.1 Soap 0.6 0.6 0.6 0.6 0.6 0.6 0.6Ethylenediamine disuccinic acid 0.1 0.1 0.1 0.1 0.1 0.1 0.1Acrylate/maleate copolymer 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Hydroxyethanedi(methylene 0.4 0.4 0.4 0.4 0.4 0.4 0.4 phosphonic acid) Mono-C₁₂₋₁₄alkyl, di-methyl, 0.5 0.5 0.5 0.5 0.5 0.5 0.5 mono-hydroyethylquaternary ammonium chloride Linear alkyl benzene 0.1 0.1 0.2 0.1 0.10.2 0.1 Linear alkyl benzene sulphonate 10.3 10.1 19.9 14.7 10.3 17 10.5Magnesium sulphate 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Sodium carbonate 19.519.2 10.1 18.5 29.9 10.1 16.8 Sodium sulphate 29.6 29.8 38.8 15.1 24.419.7 19.1 Sodium Chloride 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Zeolite 9.6 9.48.1 18 10 13.2 17.3 Photobleach particle 0.1 0.1 0.2 0.1 0.2 0.1 0.2Blue and red carbonate speckles 1.8 1.8 1.8 1.8 1.8 1.8 1.8 EthoxylatedAlcohol AE7 1 1 1 1 1 1 1 Tetraacetyl ethylene diamine 0.9 0.9 0.9 0.90.9 0.9 0.9 agglomerate (92 wt % active) Citric acid 1.4 1.4 1.4 1.4 1.41.4 1.4 PDMS/clay agglomerates (9.5% 10.5 10.3 5 15 5.1 7.3 10.2 wt %active PDMS) Polyethylene oxide 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Enzymes e.g.Protease (84 mg/g 0.2 0.3 0.2 0.1 0.2 0.1 0.2 active), Amylase (22 mg/gactive) Suds suppressor agglomerate 0.2 0.2 0.2 0.2 0.2 0.2 0.2 (12.4 wt% active) Sodium percarbonate (having 7.2 7.1 4.9 5.4 6.9 19.3 13.1 from12% to 15% active AvOx) Additional Neat Perfume** 0.5 0.5 0.5 0.5 0.50.5 0.5 Amine* 0.1 0.5 0.0 0.01 0.02 0.00 0.07 Perfume Delivery SystemAs 0.05 0.0 0.1 0.0 0.2 0.4 0.0 Disclosed In The Present SpecificationIncluding Examples 2-4 Perfume comprising one or more 0.3 0.4 0.01 0.020.04 0.1 0.1 PRMs from Table 1 Water 1.4 1.4 1.4 1.4 1.4 1.4 1.4 Misc0.1 0.1 0.1 0.1 0.1 0.1 0.1 Total Parts 100 100 100 100 100 100 100 *Oneor more materials comprising an amine moiety as disclosed in the presentspecification. **Optional

Example 7 Liquid Laundry Formulations (HDLs)

Ingredient HDL 1 HDL 2 HDL3 HDL4 HDL 5 HDL 6 Alkyl Ether Sulphate 0.000.50 12.0 12.0 6.0 7.0 Dodecyl Benzene 8.0 8.0 1.0 1.0 2.0 3.0 SulphonicAcid Ethoxylated Alcohol 8.0 6.0 5.0 7.0 5.0 3.0 Citric Acid 5.0 3.0 3.05.0 2.0 3.0 Fatty Acid 3.0 5.0 5.0 3.0 6.0 5.0 Ethoxysulfated 1.9 1.21.5 2.0 1.0 1.0 hexamethylene diamine quaternized Diethylene triaminepenta 0.3 0.2 0.2 0.3 0.1 0.2 methylene phosphonic acid Enzymes 1.200.80 0 1.2 0 0.8 Brightener (disulphonated 0.14 0.09 0 0.14 0.01 0.09diamino stilbene based FWA) Cationic hydroxyethyl 0 0 0.10 0 0.200 0.30cellulose Poly(acrylamide-co- 0 0 0 0.50 0.10 0 diallyldimethylammoniumchloride) Hydrogenated Castor Oil 0.50 0.44 0.2 0.2 0.3 0.3 StructurantBoric acid 2.4 1.5 1.0 2.4 1.0 1.5 Ethanol 0.50 1.0 2.0 2.0 1.0 1.0 1,2propanediol 2.0 3.0 1.0 1.0 0.01 0.01 Glutaraldehyde 0 0 19 ppm 0 13 ppm0 Diethyleneglycol (DEG) 1.6 0 0 0 0 0 2,3-Methyl-1,3- 1.0 1.0 0 0 0 0propanediol (M pdiol) Mono Ethanol Amine 1.0 0.5 0 0 0 0 NaOH SufficientTo pH 8 pH 8 pH 8 pH 8 pH 8 pH 8 Provide Formulation pH of: SodiumCumene 2.00 0 0 0 0 0 Sulphonate (NaCS) Silicone (PDMS) emulsion 0.0030.003 0.003 0.003 0.003 0.003 Additional Neat Perfume** 0.7 0.5 0.8 0.80.6 0.6 Amine* 0.01 0.10 0.0 0.10 0.20 0.05 Perfume comprising one or0.02 0.15 0.0 0.2 0.3 0.1 more PRMs from Table 1 Perfume Delivery System0.2 0.02 0.4 0.0 0.0 0.0 As Disclosed In The Present SpecificationIncluding Examples 2-4 Water Balance Balance Balance Balance BalanceBalance *One or more materials comprising an amine moiety as disclosedin the present specification. **Optional.

Example 8 Shampoo Formulation

Ingredient Ammonium Laureth Sulfate (AE₃S) 6.00 Ammonium Lauryl Sulfate(ALS) 10.00  Laureth-4 Alcohol 0.90 Trihydroxystearin ⁽⁷⁾ 0.10 Perfumecomprising one or more 0.60 PRMs from Table 1 Sodium Chloride 0.40Citric Acid 0.04 Sodium Citrate 0.40 Sodium Benzoate 0.25 EthyleneDiamine Tetra Acetic Acid 0.10 Dimethicone ^((9, 10, 11))   1.00 ⁽⁹⁾Water and Minors (QS to 100%) Balance

Example 9 Fine Fragrance Formulation

Ingredient 1 2 3 Cyclic oligosaccharide 0 5 10 Ethanol 90 75 80 Perfumecomprising one or more 10 20 10 PRMs from Table 1

The dimensions and values disclosed herein are not to be understood asbeing strictly limited to the exact numerical values recited. Instead,unless otherwise specified, each such dimension is intended to mean boththe recited value and a functionally equivalent range surrounding thatvalue. For example, a dimension disclosed as “40 mm” is intended to mean“about 40 mm”

All documents cited in the Detailed Description of the Invention are, inrelevant part, incorporated herein by reference; the citation of anydocument is not to be construed as an admission that it is prior artwith respect to the present invention. To the extent that any meaning ordefinition of a term in this document conflicts with any meaning ordefinition of the same term in a document incorporated by reference, themeaning or definition assigned to that term in this document shallgovern.

While particular embodiments of the present invention have beenillustrated and described, it would be obvious to those skilled in theart that various other changes and modifications can be made withoutdeparting from the spirit and scope of the invention. It is thereforeintended to cover in the appended claims all such changes andmodifications that are within the scope of this invention.

What is claimed is:
 1. A perfume raw material comprising2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 2. A perfumecomprising, based on total perfume weight, from about 0.01% to about50%, of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 3. Aconsumer product comprising, based on total consumer product weight,from about 0.0001% to about 25% of2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 4. A consumerproduct according to claim 3, said consumer product being a cleaningand/or treatment composition, said composition comprising, based ontotal composition weight, from about 0.0001% to about 25% of2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 5. A consumerproduct according to claim 3, said consumer product being a fabricand/or hard surface cleaning and/or treatment composition, saidcomposition comprising, based on total composition weight, from about0.00001% to about 25% of2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 6. A consumerproduct according to claim 3, said consumer product being a detergent,said detergent comprising, based on total detergent weight, from about0.00001% to about 25% of2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 7. A consumerproduct according to claim 3, said consumer product being a highlycompacted consumer product, said highly compacted consumer productcomprising based on total highly compacted consumer product weight, fromabout 0.00001% to about 25% of2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 8. A perfumedelivery system comprising from 0.001% to about 50% of2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol, said perfumedelivery system being a polymer assisted delivery system;molecule-assisted delivery system; fiber-assisted delivery system; amineassisted delivery system; cyclodextrin delivery system; starchencapsulated accord; inorganic carrier delivery system; or pro-perfume.9. A perfume delivery system according to claim 8, said perfume deliverysystem being nanocapsule or microcapsule comprising, based on totalnanocapsule or microcapsule weight, from about 0.1% to about 99% of2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.